Organization
Institute of Transformative Bio-Molecules Professor
Graduate School
Graduate School of Engineering
Title
Professor
External link
OOI Takashi
Research Areas
Research Areas 1
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Others / Others / Synthetic Chemistry
Current Research Project and SDGs
Current Research Project and SDGs 1
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有機イオン対の分子設計に基づく触媒機能の創出
Research History
Research History 8
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Institute of Transformative Bio-Molecules (ITbM) Professor
2013.4
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Country：Japan
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Professor (Nagoya University)
2006.5
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Associate Professor (Kyoto University)
2001.1 - 2006.4
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Country：Japan
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Lecturer (Hokkaido University)
1998.6 - 2000.12
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Country：Japan
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Assistant Professor (Hokkaido University)
1995.6 - 1998.5
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Country：Japan
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Postdoctoral Fellow (MIT)
1994.6 - 1995.3
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Research Fellow (PD) of the Japan Society for the Promotion of Science for Young Scientists
1994.4 - 1995.5
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Country：Japan
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Research Fellow (DC) of the Japan Society for the Promotion of Science for Young Scientists
1992.1 - 1994.3
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Country：Japan
Education
Education 2
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Nagoya University Graduate School, Division of Engineering Department of Applied Chemistry
1991.4 - 1994.3
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Country： Japan
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Nagoya University Graduate School, Division of Engineering Department of Applied Chemistry
1989.4 - 1991.3
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Country： Japan
Professional Memberships
Professional Memberships 3
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Chemical Society of Japan
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The Society of Synthetic Organic Chemistry, Japan
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American Chemical Society
Committee Memberships
Committee Memberships 4
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独立行政法人日本学術振興会学術システム研究センター 専門研究員
2023.4 - 2026.3
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井上科学振興財団 選考委員会委員
2022.4
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有機合成化学協会 東海支部支部長
2021.3 - 2023.2
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Committee type：Academic society
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日本学術振興会 先端科学シンポジウム事業委員
2020.4
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Committee type：Government
Awards
Awards 11
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有機合成化学協会研究企画賞
1996 有機合成化学協会
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Country：Japan
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日本化学会進歩賞
1999 日本化学会
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Country：Japan
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Theme Journal Award
2006 Theme
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Country：Japan
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日本学術振興会賞
2011.3 日本学術振興会
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Country：Japan
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第25回日本IBM科学賞
2011.11 日本IBM
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Country：Japan
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Inoue Prize for Science
2014.2
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Country：Japan
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Fellow of the Royal Society of Chemistry
2014 Fellow of the Royal Society of Chemistry
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有機合成化学協会企業冠賞
2017 有機合成化学協会企業冠賞
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第一三共・創薬有機化学賞
2017 第一三共
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日本化学会賞
2020.11 日本化学会
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Award type：Award from Japanese society, conference, symposium, etc.
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Swiss Chemical Society Lectureship
2019.5 Swiss Chemical Society
Papers
Papers 203
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Photocatalytic carbyne reactivity of phosphorus ylides for three-component formal cycloaddition reactions Reviewed International coauthorship
Ryuhei Suzuki, Taiga Ando, Fritz Deufel, Kohsuke Ohmatsu, and Takashi Ooi
Nature Synthesis Vol. 3 page： 1385 - 1391 2024.7
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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p-Diarylboryl Halothiophenols as Multifunctional Catalysts via Photoactive Intramolecular Frustrated Lewis Pairs Reviewed Open Access
Takeru Kikura, Yuya Taura, Yoshitaka Aramaki, and Takashi Ooi
Journal of the American Chemical Society Vol. 146 ( 29 ) page： 20425 - 20431 2024.7
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1021/jacs.4c06122
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Zwitterionic Acridinium Amidate: A Nitrogen-Centered Radical Catalyst for Photoinduced Direct Hydrogen Atom Transfer Reviewed International coauthorship Open Access
Lukas Entgelmeier, Soichiro Mori, Shion Sendo, Rie Yamaguchi, Ryuhei Suzuki, Takeshi Yanai, Olga García Mancheño, Kohsuke Ohmatsu, and Takashi Ooi
Angewandte Chemie International Edition Vol. 63 ( 43 ) page： e202404890 2024.6
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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If the Crown Fits: Sterically Demanding N-Heterocyclic Carbene Promotes the Formation of Au8Pt Nanocluster Reviewed International coauthorship
Joseph F. DeJesus, Samuel I. Jacob, Quan Manh Phung, Koichi Mimura, Yoshitaka Aramaki, Takashi Ooi, Masakazu Nambo, Cathleen M. Crudden
Journal of the American Chemical Society Vol. 146 ( 34 ) page： 23806 - 23813 2024.8
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Catalytic 1,1-Cyanoalkylation of Electron-Deficient Olefins Reviewed
Kohsuke Ohmatsu, Duc An Truong, Shohei Morita, Keiji Maruoka, and Takashi Ooi
Organic Letters Vol. 26 ( 19 ) page： 4055 - 4058 2024.5
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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大井 貴史
有機合成化学協会誌 Vol. 81 ( 10 ) page： 929 - 929 2023.10
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Language：Japanese Publishing type：Research paper (scientific journal) Publisher：公益社団法人 有機合成化学協会
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Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis Invited Reviewed
Yoshitaka Aramaki, Yuki Uchida, Ryo Ishikawa, and Takashi Ooi
Journal of Photochemistry and Photobiology 2023.8
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Catalytic Formal Carbyne Transformation of Phosphorus Ylides Reviewed
Ryuhei Suzuki, Taiga Ando, Fritz Deufel, Kohsuke Ohmatsu, and Takashi Ooi
ChemRxiv 2023.8
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Zwitterionic Diphenylphosphinyl Amidate as a Powerful Photoinduced Hydrogen-Atom-Transfer Catalyst for C-H Alkylation of Simple Alkanes. Reviewed
Ohmatsu K, Suzuki R, Fujita H, Ooi T
The Journal of organic chemistry Vol. 88 ( 10 ) page： 6553 - 6556 2023.5
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Authorship：Last author, Corresponding author Language：English Publishing type：Research paper (scientific journal)
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Hydrogen-Atom Transfer Catalysis for C–H Alkylation of Benzylic Fluorides Reviewed
Kohsuke Ohmatsu, Hiroki Fujita, Ryuhei Suzuki, Takashi Ooi
2022.4
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In Silico Analysis and Synthesis of Nafamostat Derivatives and Evaluation of Their Anti-SARS-CoV-2 Activity Reviewed
Fujimoto KJ, Hobbs DCF, Umeda M, Nagata A, Yamaguchi R, Sato Y, Sato A, Ohmatsu K, Ooi T, Yanai T, Kimura H, Murata T
Viruses Vol. 14 ( 2 ) page： 389 2022.2
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Thioamidate Ion as Effective Cocatalyst for Photoinduced C–H Alkylation via Multisite Proton-coupled Electron Transfer Reviewed
Kohsuke Ohmatsu ,Haruka Fujimori ,Kodai Minami ,Kosuke Nomura ,Mari Kiyokawa , and Takashi Ooi
2022.2
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DOI： 10.1246/cl.220026
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Hydrogen-Atom-Transfer-Mediated Acceptorless Dehydrogenative Cross-Coupling Enabled by Multiple Catalytic Functions of Zwitterionic Triazolium Amidate Reviewed
Kodai Minami, Kohsuke Ohmatsu, and Takashi Ooi
ACS Catalysis Vol. 12 ( 3 ) page： 1971 - 1976 2022.1
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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Catalytic Asymmetric Strecker Reaction of Ketoimines with Potassium Cyanide Reviewed
Kohsuke Ohmatsu, Yusuke Morita, Mari Kiyokawa, Kimihiro Hoshino, and Takashi Ooi
Asian Journal of Organic Chemistry Vol. 10 ( 12 ) page： 3237 - 3240 2021.10
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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o-Quinone methide with overcrowded olefinic core as a catalytically-active surrogate of triarylmethylium salt for dehydridative oxidationof benzylic alcohols under aerobic photoirradiation conditions Reviewed
Kohsuke Kato, Daisuke Uraguchi, and Takashi Ooi
Tetrahedron Vol. 100 ( 5 ) page： 132459 2021.9
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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o-Quinone methide with overcrowded olefinic core as a catalytically-active surrogate of triarylmethylium salt for dehydridative oxidation of benzylic alcohols under aerobic photoirradiation conditions Reviewed
Kohsuke Kato, Daisuke Uraguchi, Takashi Ooi
Tetrahedron 2021.9
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Synthesis and enantioseparation of chiral Au<sub>13</sub> nanoclusters protected by bis-<i>N</i>-heterocyclic carbene ligands Reviewed
Yi H, Osten KM, Levchenko TI, Veinot AJ, Aramaki Y, Ooi T, Nambo M, Crudden CM
Chemical science Vol. 12 ( 31 ) page： 10436 - 10440 2021.8
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/d1sc03076k
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Catalytic Asymmetric Cyanoalkylation of Electron-Deficient Olefins with Potassium Cyanide and Alkyl Halides Reviewed
Kohsuke Ohmatsu, Yusuke Morita, Mari Kiyokawa, Takashi Ooi
Journal of the American Chemical Society Vol. 143 ( 29 ) page： 11218 - 11224 2021.7
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1021/jacs.1c05380
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Synthesis and enantioseparation of chiral Au13 nanoclusters protected by bis-N-heterocyclic carbene ligands Reviewed
Hong Yi, Kimberly M. Osten, Tetyana I. Levchenko, Alex J. Veinot, Yoshitaka Aramaki, Takashi Ooi, Masakazu Nambo and Cathleen M. Crudden
Chemical Science 2021.7
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DOI： 10.1039/D1SC03076K
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Exploiting Transient Radical Cations as Brønsted Acids for Allylic C-H Heteroarylation of Enol Silyl Ethers Reviewed
Tsubasa Nakashima, Haruka Fujimori, Kohsuke Ohmatsu , Takashi Ooi
Chemistry-A European Journal Vol. 27 ( 36 ) page： 9253 - 9256 2021.6
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
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Daisuke Uraguchi, Takashi Ooi
Journal of Synthetic Organic Chemistry, Japan Vol. 79 ( 5 ) page： 406 - 416 2021.5
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Society of Synthetic Organic Chemistry, Japan
<p>Simultaneous control of multiple selectivity is a powerful means for constructing structurally discrete, functionalized building blocks, yet it has remained a challenging task in organic synthesis and catalysis. We have tackled this objective by taking advantage of the unique ability of <i>P</i>-spiro chiral tetraaminophosphonium ion to control transition-state structures of the target reaction. Namely, the use of its conjugate base, chiral iminophosphorane, as an organic base catalyst allowed for the rigorous control of not only enantioselectivity but also additional selectivity associated with other factors, such as geometry, regiochemistry, diastereomer formation, and reaction pathway, in various carbon-carbon bond-forming reactions. Theoretical investigation revealed key elements to achieve the multiple selectivity control, which would provide a basis for the development of related and more effective catalytic systems.</p>
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Catalytic asymmetric synthesis of 5-membered alicyclic α-quaternary β-amino acids <i>via</i> [3 + 2]-photocycloaddition of α-substituted acrylates Reviewed
Yuto Kimura, Daisuke Uraguchi, Takashi Ooi
Organic & Biomolecular Chemistry Vol. 19 ( 8 ) page： 1744 - 1747 2021.3
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Authorship：Last author, Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/d1ob00126d
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Catalytic Asymmetric Synthesis of 5-Membered Alicyclic α-Quaternary β-Amino Acids via [3+2]-Photocycloaddition of α-Substituted Acrylates Reviewed
Organic & Biomolecular Chemistry 2021.2
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DOI： 10.1039/D1OB00126D
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o-Quinone Methide with Overcrowded Olefin Component as a Dehydridation Catalyst under Aerobic Photoirradiation Conditions Reviewed
CHEMICAL SCIENCE Vol. 12 page： 2778-2783 2021.1
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Authorship：Last author, Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/D0SC06240E
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Mannich-type allylic C-H functionalization of enol silyl ethers under photoredox-thiol hybrid catalysis Reviewed
Tsubasa Nakashima, Kohsuke Ohmatsu, Takashi Ooi
ORGANIC & BIOMOLECULAR CHEMISTRY Vol. 19 ( 1 ) page： 141 - 145 2021.1
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Authorship：Last author, Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/d0ob01862g
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Hybrid Catalysis of 8-Quinolinecarboxaldehyde and Br?nsted Acid for Efficient Racemization of α-Amino Amides and Its Application in Chemoenzymatic Dynamic Kinetic Resolution Reviewed
HETEROCYCLES Vol. 2021 ( 103 ) page： xxxx-xxxx 2021
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Urea as a Redox-Active Directing Group under Asymmetric Photocatalysis of Iridium-Chiral Borate Ion Pairs Reviewed
Uraguchi Daisuke, Kimura Yuto, Ueoka Fumito, Ooi Takashi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 142 ( 46 ) page： 19462 - 19467 2020.11
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DOI： 10.1021/jacs.0c09468
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Redox-regulated divergence in photocatalytic addition of alpha-nitro alkyl radicals to styrenes Reviewed
Tsuchiya Yuto, Onai Ryota, Uraguchi Daisuke, Ooi Takashi
CHEMICAL COMMUNICATIONS Vol. 56 ( 75 ) page： 11014 - 11017 2020.9
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DOI： 10.1039/d0cc04821f
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Redox-Regulated Divergence in Photocatalytic Addition of α-Nitro Alkyl Radicals to Styrenes Reviewed
Yuto Tsuchiya, Ryota Onai, Daisuke Uraguchi and Takashi Ooi
Chemical Communications 2020.8
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DOI： 10.1039/D0CC04821F
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A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis Reviewed
Uraguchi Daisuke, Ueoka Fumito, Tanaka Naoya, Kizu Tomohito, Takahashi Wakana, Ooi Takashi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 59 page： 11456-11461 2020.7
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Non-Enzymatic Hybrid Catalysis for Stereoconversion of l-Amino Acid Derivatives to d-Isomers Reviewed
Nagato Yuya, Kiyokawa Mari, Ueki Yusuke, Kikuchi Jun, Ohmatsu Kohsuke, Terada Masahiro, Ooi Takashi
ASIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 9 ( 4 ) page： 561-565 2020.4
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Exploiting single-electron transfer in Lewis pairs for catalytic bond-forming reactions Reviewed
Aramaki Yoshitaka, Imaizumi Naoki, Hotta Mao, Kumagai Jun, Ooi Takashi
CHEMICAL SCIENCE Vol. 11 ( 17 ) page： 4305-4311 2020.3
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Authorship：Last author, Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/d0sc01159b
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Unveiling Latent Photoreactivity of Imines Reviewed
Uraguchi Daisuke, Tsuchiya Yuto, Ohtani Tsuyoshi, Enomoto Takafumi, Masaoka Shigeyuki, Yokogawa Daisuke, Ooi Takashi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 59 ( 9 ) page： 3665-3670 2020.2
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Authorship：Last author, Corresponding author Language：English Publishing type：Research paper (scientific journal)
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Zwitterionic 1,2,3-Triazolium Amidate as a Catalyst for Photoinduced Hydrogen-Atom Transfer Radical Alkylation Reviewed
Ohmatsu Kohsuke, Suzuki Ryuhei, Furukawa Yukino, Sato Makoto, Ooi Takashi
ACS CATALYSIS Vol. 10 ( 4 ) page： 2627-2632 2020.2
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Language：English Publishing type：Research paper (scientific journal)
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Ion-paired Ligands for Palladium-catalyzed Allylic Alkylation under Base-free Conditions
Ohmatsu Kohsuke, Matsuyama Naho, Nagato Yuya, Ooi Takashi
Chemistry Letters Vol. 49 ( 9 ) page： 1114 - 1116 2020
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Publishing type：Research paper (scientific journal) Publisher：公益社団法人 日本化学会
<p>The effectiveness of a catalytic amount of bromide ions for significantly accelerating the palladium-catalyzed allylation of carbonyl compounds with allylic carbonates is reported. In particular, the utilization of an ammonium–phosphine hybrid ligand bearing a bromide ion is uniquely effective for promoting allylation under mild, base-free conditions, thus obviating the need to use polar solvents and external strong Brønsted bases.</p>
DOI： 10.1246/cl.200264
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Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues
Hayakawa Sakiho, Kawasaki Ayumi, Hong Yongseok, Uraguchi Daisuke, Ooi Takashi, Kim Dongho, Akutagawa Tomoyuki, Fukui Norihito, Shinokubo Hiroshi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 141 ( 50 ) page： 19807-19816 2019.12
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Cationic Organic Catalysts or Ligands in Concert with Metal Catalysts
Ohmatsu Kohsuke, Ooi Takashi
TOPICS IN CURRENT CHEMISTRY Vol. 377 ( 6 ) 2019.12
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Direct allylic C-H alkylation of enol silyl ethers enabled by photoredox-Bronsted base hybrid catalysis
Ohmatsu Kohsuke, Nakashima Tsubasa, Sato Makoto, Ooi Takashi
NATURE COMMUNICATIONS Vol. 10 2019.6
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Language：English Publishing type：Research paper (scientific journal)
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Photocatalytic borylcyclopropanation of alpha-boryl styrenes
Ohtani Tsuyoshi, Tsuchiya Yuto, Uraguchi Daisuke, Ooi Takashi
ORGANIC CHEMISTRY FRONTIERS Vol. 6 ( 11 ) page： 1734-1737 2019.6
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Photocatalytic Borylcyclopropanation of α-Boryl Styrenes Reviewed
Tsuyoshi Ohtani, Yuto Tsuchiya, Daisuke Uraguchi and Takashi Ooi
Org. Chem. Front. Vol. 2019 ( 6 ) page： 1734-1737 2019.6
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Language：English Publishing type：Research paper (scientific journal)
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Formal Hydroformylation of α,β-Unsaturated Carboxylic Acids under Photoexcited Ketone Catalysis Reviewed
Kailong Zhu, Tsuyoshi Ohtani, Chandra Bhushan Tripathi, Daisuke Uraguchi, and Takashi Ooi
Chem. Lett. Vol. 2019 ( 48 ) 2019
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The design principle of synthetic strigolactones
Tsuchiya Yuichiro, Uraguchi Daisuke, Ooi Takashi
Regulation of Plant Growth & Development Vol. 54 ( 1 ) page： 49-53 2019
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Language：English Publishing type：Research paper (scientific journal)
<p>Strigolactones have diverse functions as plant hormones and as ecological signals to communicate with soil microbes. Strigolactones are also exploited by parasitic plants, including noxious parasitic weeds called <i>Striga hermonthica</i>, as germination cues that enable efficient parasitism to their host plants. Recent understanding for the mechanism of strigolactone perception by α/β-hydrolase receptors has provided opportunities to dissect the diverse functions with synthetic strigolactones. Here, we introduce the design principle of the synthetic strigolactones, which relies on a hybrid of two functions encoded in the two substructures, ABC-ring and D-ring. The principle discussed here has been applied to develop a <i>Striga</i>-selective suicide germination stimulant acting at femtomolar-range.</p>
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A femto-molar range suicide germination stimulant for the parasitic plant Striga hermonthica Reviewed
Daisuke Uraguchi, Keiko Kuwata, Yuh Hijikata, Rie Yamaguchi, Hanae Imaizumi, Sathiyanarayanan AM, Christin Rakers, Narumi Mori, Kohki Akiyama, Stephan Irle, Peter McCourt, Toshinori Kinoshita, Takashi Ooi, Yuichiro Tsuchiya
Science Vol. 2018 ( 362 ) page： 1301-1305 2018.12
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Chemistry of Ammonium Betaines: Application to Ion-Pair Catalysis for Selective Organic Transformations
Uraguchi Daisuke, Ooi Takashi
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN Vol. 76 ( 11 ) page： 1144-1153 2018.11
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Protonated Bis-1,2,3-triazole as an Anion-Binding Chiral Bronsted Acid for Catalytic Asymmetric Friedel-Crafts Reaction of Indoles with Imines
Furukawa Yukino, Suzuki Ryuhei, Nakashima Tsubasa, Gramage-Doria Rafael, Ohmatsu Kohsuke, Ooi Takashi
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN Vol. 91 ( 8 ) page： 1252-1257 2018.8
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Language：English Publishing type：Research paper (scientific journal)
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Catalyst-Directed Guidance of Sulfur-Substituted Enediolates to Stereoselective Carbon-Carbon Bond Formation with Aldehydes
Uraguchi Daisuke, Yamada Kohei, Sato Makoto, Ooi Takashi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 140 ( 15 ) page： 5110-5117 2018.4
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Catalyst-Enabled Site-Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors
Uraguchi Daisuke, Shibazaki Ryo, Tanaka Naoya, Yamada Kohei, Yoshioka Ken, Ooi Takashi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 57 ( 17 ) page： 4732-4736 2018.4
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Language：English Publishing type：Research paper (scientific journal)
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Allenedicarboxylate as a Stereochemically Labile Electrophile for Chiral Organic Base-catalyzed Stereoselective Michael Addition
Uraguchi Daisuke, Kawai Yasutaka, Sasaki Hitoshi, Yamada Kohei, Ooi Takashi
CHEMISTRY LETTERS Vol. 47 ( 4 ) page： 594-597 2018.4
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Molecular Design, Synthesis, and Asymmetric Catalysis of a Hexacoordinated Chiral Phosphate Ion Reviewed
Daisuke Uraguchi, Hitoshi Sasaki, Yuto Kimura, Takaki Ito, and Takashi Ooi
J. Am. Chem. Soc. Vol. 2018 ( 140 ) page： 2765-2768 2018.2
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大井 貴史
有機合成化学協会誌 Vol. 76 ( 6 ) page： 565-565 2018
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Language：English Publishing type：Research paper (scientific journal)
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Diastereo- and enantioselective phase-transfer alkylation of 3-substituted oxindoles with racemic secondary alkyl halides Reviewed
Kohsuke Ohmatsu, Yukino Furukawa, Mari Kiyokawa and Takashi Ooi
Chem. Commun. Vol. 2017 ( 53 ) page： 13113-13116 2017.10
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Determination of the absolute configuration of compounds bearing chiral quaternary carbon centers using the crystalline sponge method
Shiho Sairenji, Takashi Kikuchi, Mohamed Ahmed Abozeid, Shinobu Takizawa, Hiroaki Sasai, Yuichiro Ando, Kohsuke Ohmatsu, Takashi Ooi and Makoto Fujita
Chem. Sci. Vol. 2017 ( 8 ) page： 5132-5136 2017.8
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Photoredox Ketone Catalysis for Direct C-H Imidation and Acyloxylation of Arenes Reviewed
Chandra Bhushan Tripathi, Tsuyoshi Ohtani, Michael T. Corbett and Takashi Ooi
Chem. Sci. ( 8 ) page： 5622-5627 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/C7SC01700F
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N-Sulfonyl α-Imino Ester-Derived Chiral Oxaziridines: Catalytic Asymmetric Synthesis and Application as a Modular Chiral Organic Oxidant Reviewed
Naoya Tanaka, Ryosuke Tsutsumi, Daisuke Uraguchi,Takashi Ooi
Chem. Commun. ( 53 ) page： 6999-7002 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/C7CC02502E
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Unique Site-selectivity Control in Asymmetric Michael Addition of Azlactone to Alkenyl Dienyl Ketones Enabled by P-Spiro Chiral Iminophosphorane Catalysis Invited Reviewed
Ken Yoshioka, Kohei Yamada, Daisuke Uraguchi,Takashi Ooi
Chem. Commun. ( 53 ) page： 5495-5498 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/C7CC01715D
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Acridinium Betaine as a Single-Electron-Transfer Catalyst: Design and Application to Dimerization of Oxindoles Reviewed
Daisuke Uraguchi, Masahiro Torii, Takashi Ooi
ACS Catal. ( 7 ) page： 2765-2769 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
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Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst Reviewed
Daisuke Uraguchi, Ken Yoshioka, Takashi Ooi
Nature Communications ( 8 ) page： 14793 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1038/ncomms14793
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[5.5]-P-Spirocyclic Chiral Triaminoiminophosphorane-Catalyzed Asymmetric Hydrophosphonylation of Aldehydes and Ynones Reviewed
Daisuke Uraguchi, Takaki Ito, Yuto Kimura, Yumiko Nobori, Makoto Sato, Takashi Ooi
Bull. Chem. Soc. Jpn. ( 90 ) page： 546-555 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
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In Situ Electrophilic Activation of Hydrogen Peroxide for Catalytic Asymmetric α-Hydroxylation of 3-Substituted Oxindoles Invited Reviewed
Kohsuke Ohmatsu, Yuichiro Ando, Takashi Ooi
Synlett ( 28 ) page： 1291-1294 2017
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Stereoselective Aza-Henry Reaction of 3-Nitro-Dihydro-2(1H)-Quinolones with N-BOC-Aldimines under the Catalysis of Chiral Ammonium Betaines Invited Reviewed
Daisuke Uraguchi, Masahiro Torii, Kohsuke Kato, Takashi Ooi
Heterocycles ( 94 ) page： 441-447 2017
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Authorship：Lead author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.3987/COM-16-13642
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Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study Reviewed
Yamanaka, Masahiro; Sakata, Ken; Yoshioka, Ken; Uraguchi, Daisuke; Ooi, Takashi
J. Org. Chem. Vol. 2017 ( 82 ) page： 541-548 2017
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A Modular Strategy for the Direct Catalytic Asymmetric α-Amination of Carbonyl Compound Reviewed
Kohsuke Ohmatsu, Yuichiro Ando, Tsubasa Nakashima, Takashi Ooi
Chem Vol. 1 ( 5 ) page： 802-810 2016.11
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Language：English Publishing type：Research paper (scientific journal)
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Palladium-Catalyzed Branch-Selective Decarboxylative Allylation Using Ion-Paired Ligands Reviewed
Yoshiyuki Hara, Yuya Kusano, Kohsuke Ohmatsu, and Takashi Ooi
Chem. Lett. Vol. 2016 ( 45 ) page： 552-554 2016
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Anion-Stoichiometry-Dependent Selectivity Enhancement in Ion-Paired Chiral Ligand-Palladium Complex Catalyzed Enantioselective Allylic Alkylation Reviewed
Kohsuke Ohmatsu, Yoshiyuki Hara, Yuya Kusano, Takashi Ooi
Synlett Vol. 2016 ( 27 ) page： 1047-1050 2016
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Multiple Absolute Stereocontrol in Pd-Catalyzed [3+2] Cycloaddition of Oxazolidinones and Trisubstituted Alkenes Using Chiral Ammonium-Phosphine Hybrid Ligands Reviewed
Naomichi Imagawa, Yuya Nagato, Kohsuke Ohmatsu, and Takashi Ooi
Bull. Chem. Soc. Jpn. Vol. 2016 ( 89 ) page： 649-656 2016
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Independence from the Sequence of Single-Electron Transfer of Photoredox Process in Redox-Neutral Asymmetric Bond-Forming Reaction Reviewed
Tomohito Kizu, Daisuke Uraguchi, and Takashi Ooi
J. Org. Chem. Vol. 2016 ( 81 ) page： 6953-6958 2016
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Chiral Ammonium Betaine-Catalyzed Asymmetric Mannich-Type Reaction of Oxindoles Reviewed
Masahiro Torii, Kohsuke Kato, Daisuke Uraguchi, and Takashi Ooi
Beilstein J. Org. Chem. Vol. 2016 ( 12 ) page： 2099-2103 2016
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Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines Reviewed
Daisuke Uraguchi, Natsuko Kinoshita, Tomohito Kizu, and Takashi Ooi
J. Am. Chem. Soc. Vol. 2015 ( 137 ) page： 13768-13771 2015
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Vinylogy in Nitronates: Utilization of α-Aryl Conjugated Nitroolefins as a Nucleophile for Highly Stereoselective Aza-Henry Reaction Reviewed
Keigo Oyaizu, Daisuke Uraguchi, Takashi Ooi
Chem. Commun. Vol. 2015 ( 51 ) page： 4437-4439 2015
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Highly E- and Enantioselective Michael Addition to Electron-deficient Internal Alkynes under the Catalysis of Chiral Iminophosphorane Reviewed
Daisuke Uraguchi, Kohei Yamada, Takashi Ooi
Angew. Chem. Int. Ed. Vol. 2015 ( 54 ) page： 9954-9957 2015
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Catalytic Asymmetric Cyanation of Alkylideneindolenines Generated from Sulfonylalkylindoles Reviewed
Kohsuke Ohmatsu, Yukino Furukawa, Daigo Nakaguro, and Takashi Ooi
Chem. Lett. Vol. 2015 ( 44 ) page： 1350-1352 2015
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Enantioselective Reductive Multicomponent Coupling Reactions between Isatins and Aldehydes Reviewed
Matthew A. Horwitz, Naoya Tanaka, Takuya Yokosaka, Daisuke Uraguchi, Jeffrey S. Johnson, and Takashi Ooi
Chem. Sci. Vol. 2015 ( 6 ) page： 6086-6090 2015
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Ligand-enabled multiple absolute stereocontrol in metal-catalysed cycloaddition for construction of contiguous all-carbon quaternary stereocentres Reviewed
Kohsuke Ohmatsu, Naomichi Imagawa, Takashi Ooi
Kohsuke Ohmatsu, Naomichi Imagawa, Takashi Ooi Vol. 6 ( 1 ) page： 47-51 2014
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Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition of 5-Vinyloxazolidinones with Imines Using Chiral Ammonium-Phosphine Hybrid Ligand Reviewed
Kohsuke Ohmatsu, Shinya Kawai, Naomichi Imagawa, Takashi Ooi
ACS Catal. Vol. 2014 ( 4 ) page： 4304-4306 2014
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Catalytic asymmetric Payne oxidation under the catalysis of P-spiro chiral triaminoiminophosphorane: Application to the synthesis of N-sulfonyl oxaziridines Reviewed
Daisuke Uraguchi, Ryosuke Tsutsumi, Takashi Ooi
Tetrahedron Vol. 2014 ( 70 ) page： 1691-1701 2014
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Asymmetric Alkylation of α-Cyanosulfones Catalyzed by Chiral 1,2,3-Triazolium Salts Reviewed
Kohsuke Ohmatsu, Yusuke Hakamata, Ayano Goto, Takashi Ooi
Heterocycles Vol. 2014 ( 88 ) page： 1661-1666 2014
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Ligand-controlled E/Z selectivity and enantioselectivity in palladium-catalyzed allylation of benzofuranones with 1,2-disubstituted allylic carbonates Reviewed
Kohsuke Ohmatsu, Mitsunori Ito , Takashi Ooi
Chem. Commun. Vol. 2014 ( 50 ) page： 4554-4557 2014
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Practical Preparation of Chiral N-Sulfonyl Oxaziridines by Catalytic Asymmetric Payne Oxidation Reviewed
Ryosuke Tsutsumi, Seonwoo Kim, Daisuke Uraguchi, Takashi Ooi
Synthesis (PSP article) Vol. 2014 ( 46 ) page： 871-878 2014
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Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction-Julia-Kocienski olefination sequence Reviewed
Daisuke Uraguchi, Shinji Nakamura, Hitoshi Sasaki, Yuki Konakade, Takashi Ooi
Chem. Commun. Vol. 2014 ( 50 ) page： 3491-3493 2014
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In-Situ Generation of Ion-Paired Chiral Ligands: Rapid Identification of Optimal Ligand for Palladium-Catalyzed Asymmetric Allylation Reviewed
Kohsuke Ohmatsu, Yoshiyuki Hara, Takashi Ooi
Chem. Sci. Vol. 2014 ( 5 ) page： 3645-3650 2014
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Enantioselective Protonation of α-Hetero Carboxylic Acid-Derived Ketene Disilyl Acetals under Chiral Ionic Brønsted Acid Catalysis Reviewed
Daisuke Uraguchi, Tomohito Kizu, Yuki Ohira, Takashi Ooi
Chem. Commun. Vol. 2014 ( 50 ) page： 13489-13491 2014
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Chiral Ammonium Betaine-Catalyzed Highly Stereoselective Aza-Henry Reaction of α-Aryl Nitromethanes with Aromatic N-Boc Imines Reviewed
Daisuke Uraguchi, Keigo Oyaizu, Haruhiro Noguchi, Takashi Ooi
Chem. Asian J. Vol. 2014 ( 10 ) page： 334-337 2014
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Uraguchi, Daisuke; Ueki, Yusuke; Sugiyama, Atsushi; Ooi, Takashi
Chem. Sci. Vol. 4 page： in press 2013.1
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A catalyst-controlled, geometrically divergent asymmetric Michael addition of azlactones to methyl propiolate has been achieved under the catalysis of P-spiro chiral triaminoiminophosphoranes. An uncommon O-protonation of the intermediary allenic enolate is proposed to rationalize geometric control and its validity is proven by the development of highly Z- and enantioselective Michael addition of azlactones to cyanoacetylene with broad substrate scope.
DOI： 10.1039/C2SC22027J
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Carbene Transfer from Triazolylidene Gold Complexes as a Potent Strategy for Inducing High Catalytic Activity Reviewed
Daniel Canseco-Gonzalez, Ana Petronilho, Helge Mueller-Bunz, Kohsuke Ohmatsu, Takashi Ooi, Martin Albrecht
J. Am. Chem. Soc. Vol. 135 ( 35 ) page： 13193-13203 2013
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Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3-Substituted Oxindoles Reviewed
Kohsuke Ohmatsu, Yuichiro Ando, Takashi Ooi
J. Am. Chem. Soc. Vol. 135 ( 50 ) page： 18706-18709 2013
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Catalytic Asymmetric Oxidation of N-Sulfonyl Imines with Hydrogen Peroxide-Trichloroacetonitrile System Reviewed
Daisuke Uraguchi, Ryosuke Tsutsumi, and Takashi Ooi
J. Am. Chem. Soc. Vol. 2013 ( 135 ) page： 8161-8164 2013
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Kohsuke Ohmatsu, Mitsunori Ito, Tomoatsu Kunieda, and Takashi Ooi
J. Am. Chem. Soc. Vol. 135 ( 2 ) page： 590–593 2012.12
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A highly enantioselective allylation of benzofuran-2(3H)-ones is achieved under Pd catalysis by taking full advantage of the structural modularity of ion-paired chiral ligands.
DOI： 10.1021/ja312125a
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Uraguchi, Daisuke; Yoshioka, Ken; Ueki, Yusuke; Ooi, Takashi
J. Am. Chem. Soc. Vol. 134 ( 47 ) page： 19370–19373 2012.11
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A vinylog of Michael addition (1,6-addition) of azlactones to δ-substituted dienyl N-acylpyrroles has been developed with virtually complete 1,6-, diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8-addition) of azlactones to ζ-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.
DOI： 10.1021/ja310209g
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Uraguchi, Daisuke; Kinoshita, Natsuko; Nakashima, Daisuke; Ooi, Takashi
Chem. Sci. Vol. 3 ( 11 ) page： 3161-3164 2012.7
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A highly enantioselective sulfa-Michael addition to aromatic and aliphatic nitroolefins is achieved under the synergistic catalysis of chiral, ionic Brønsted acid homo-1b·HBArF and 2,6-lutidine. The potential utility of this new method is clearly demonstrated by its application to the syntheses of a novel, optically active taurine derivative and β-sultam.
DOI： 10.1039/C2SC20698F
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Uraguchi, Daisuke; Oyaizu, Keigo; Ooi, Takashi
Chem. Eur. J. Vol. 18 ( 27 ) page： 8306–8309 2012.7
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Vinylogous nitronate was successfully generated from β,β-disubstituted nitroolefins for achieving a highly regio-, diastereo-, and enantioselective aza Henry reaction under the influence of chiral ammonium betaine of type 1 as an organic-base catalyst. The present approach greatly expands the synthetic utility of nitroolefins in the development of carbon-carbon bond-forming reactions.
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Catalytic Asymmetric Mannich-Type Reactions of α-Cyano α-Sulfonyl Carbanions Invited Reviewed
Ohmatsu, Kohsuke; Goto, Ayano; Ooi, Takashi
Chem. Commun. Vol. 48 ( 64 ) page： 7913-7915 2012.5
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An efficient asymmetric Mannich-type reaction of α-cyano α-sulfonyl carbanions has been achieved by exploiting the structural modularity and anion-recognition ability of chiral 1,2,3-triazolium ions. This protocol has proven to be applicable to a variety of N-Boc imines and cyanosulfones, affording β-amino α-cyanosulfones in excellent yields with high stereoselectivities.
DOI： 10.1039/C2CC32398B
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Ohmatsu, Kohsuke; Hamajima, Yuta; Ooi, Takashi
J. Am. Chem. Soc. Vol. 134 ( 21 ) page： 8794–8797 2012.5
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Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported.
DOI： 10.1021/ja3028668
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Uraguchi, Daisuke; Koshimoto, Kyohei; Ooi, Takashi
J. Am. Chem. Soc. Vol. 134 ( 16 ) page： 6972–6975 2012.4
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A new strategy for developing stereoselective bond-forming reactions is introduced; it takes advantage of the ionic nucleophilic catalysis of chiral ammonium betaines to utilize vinylic esters simultaneously as the enolate precursor and the acylating agent for coupling with electrophiles. Its synthetic utility is clearly demonstrated by the realization of a highly diastereo- and enantioselective aldol reaction from oxindole-derived vinylic carbonates.
DOI： 10.1021/ja3022939
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Base-Catalyzed Direct Aldolization of α-Alkyl-α-Hydroxy Trialkyl Phosphonoacetates Reviewed
Corbett, Michael; Uraguchi, Daisuke; Ooi, Takashi; Johnson, Jeffrey
Angew. Chem. Int. Ed. Vol. 51 ( 19 ) page： 4685–4689 2012.4
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Pass the P: Catalytic direct aldol addition of α-hydroxy trialkyl phosphonacetates to aldehydes affords α-hydroxy-β-phosphonyloxy ester products. The fully substituted glycolate enolate intermediate is generated in situ under mild conditions by a [1,2] phosphonate-phosphate rearrangement. High enantioselectivity and dramatic enhancement of reaction diastereocontrol is realized by the application of chiral iminophosphorane catalysts.
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Ion-paired chiral ligands for asymmetric palladium catalysis Reviewed
Ohmatsu, Kohsuke; Ito, Mitsunori; Kunieda, Tomoatsu; Ooi, Takashi
Nature Chemistry Vol. 4 page： 473–477 2012.4
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Conventional chiral ligands rely on the use of a covalently constructed, single chiral molecule embedded with coordinative functional groups. Here, we report a new strategy for the design of a chiral ligand for asymmetric transition-metal catalysis; our approach is based on the development of an achiral cationic ammonium-phosphine hybrid ligand paired with a chiral binaphtholate anion. This ion-paired chiral ligand imparts a remarkable stereocontrolling ability to its palladium complex, which catalyses a highly enantioselective allylic alkylation of α-nitrocarboxylates. By exploiting the possible combinations of the achiral onium entities with suitable coordinative functionalities and readily available chiral acids, this approach should contribute to the development of a broad range of metal-catalysed, stereoselective chemical transformations.
DOI： 10.1038/nchem.1311
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Highly Stereoselective Catalytic Conjugate Addition of Acyl Anion Equivalent to Nitroolefins Reviewed
Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi
Chem. Sci. Vol. 3 ( 3 ) page： 842-845 2011.11
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Highly enantioselective conjugate addition of 2-unsubstituted azlactone 3 to various nitroolefins 4 was accomplished by the selective utilization of supramolecularly assembled, chiral tetraaminophosphonium aryloxide-arylhydroxide 1a·[2a]2 as a requisite catalyst. The key to this achievement is the polarity dependence of the molecular associations of type 1·[2]n and the crucial role of the proximal arylhydroxide 2 as a proton donor. The present method offers an attractive route to various optically active amino carbonyl compounds including β2-amino acids.
DOI： 10.1039/C1SC00678A
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Enantioselective Aza-Michael Addition to Conjugated Nitroenynes Catalyzed by Chiral Arylaminophosphonium Barfates Invited Reviewed
Uraguchi, Daisuke; Kinoshita, Natsuko; Kizu, Tomohito; Ooi, Takashi
Synlett ( 9 ) page： 1265-1267 2011.4
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Enantioselective aza-Michael addition to conjugated nitroenynes has been developed. P-Spiro heterochiral arylaminophosphonium barfate 1bBArF effectively catalyzes the reaction, and the corresponding conjugate adducts, β-amino homopropargylic nitro compounds, are obtained in good chemical yields with high enantioselectivities.
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Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles Reviewed
Ohmatsu, Kohsuke, Kiyokawa, Mari, Ooi, Takashi
J. Am. Chem. Soc. ( 133 ) page： 1307–1309 2011
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Controlled Assembly of Chiral Tetraaminophosphonium Aryloxide Arylhydroxide(s) in Solution Reviewed
Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi
Angew. Chem. Int. Ed. ( 50 ) page： 3681–3683 2011
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Precise Control of Spontaneous Molecular Assembly of Chiral Tetraaminophosphonium Aryloxide-Arylhydroxide(s) in Solution Reviewed
Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi
Angew. Chem. Int. Ed. Vol. 2011 ( 50 ) page： 3681-3683 2011
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Development of P-Spiro Chiral Aminophosphonium Salts as a New Class of Versatile Organic Molecular Catalyst Reviewed
Uraguchi, Daisuke; Ooi, Takashi
有機合成化学協会誌 Vol. 68 page： 1185-1194 2010.11
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Flexible Synthesis, Structural Determination, and Synthetic Application of a New C1-Symmetric Chiral Ammonium Betaine Reviewed
Uraguchi, Daisuke; Koshimoto, Kyohei; Ooi, Takashi
Chem. Commun. Vol. 46 page： 300-302 2010
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A C1-symmetric chiral ammonium betaine has been developed, and its intramolecular ion-pairing structure in solid state and its catalytic performance to achieve the highly stereoselective Mannich-type reaction of 2-alkoxythiazol-5(4H)-ones are revealed.
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Performance of C1-symmetric chiral ammonium betaines as a catalyst for the enantioselective Mannich-type reaction of α-nitrocarboxylates Invited Reviewed
Uraguchi, Daisuke; Koshimoto, Kyohei; Sanada, Chisato; Ooi, Takashi
Tetrahedron: Asymmetry Vol. 21 page： 1189-1190 2010
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The catalytic performance of C1-symmetric chiral ammonium betaines in the enantioselective direct Mannich-type reaction of α-nitrocarboxylates with N-Boc imines has been investigated. The most effective catalyst structure has been identified; this provides a reliable synthetic route to a variety of enantiomerically enriched α-tetrasubstituted α,β-diamino acid derivatives.
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Phase-Transfer-Catalyzed Asymmetric Alkylation of α-Benzoyloxy-β-keto Esters: Stereoselective Construction of Congested 2,3-Dihydroxycarboxylic Acid Esters Reviewed
Hashimoto, Takuya; Sasaki, Keigo; Fukumoto, Kazuhiro; Murase, Yuichi; Abe, Naoyuki; Ooi, Takashi; Maruoka, Keiji
Chem. Asian J. Vol. 5 page： 562-570 2010
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Highly enantioselective phase-transfer-catalyzed alkylation of tert-butyl 2-benzoyloxy-3-oxobutanoate was realized by the use of an N-spiro chiral quaternary ammonium salt, as a complementary approach to the asymmetric hydroxylation of -alkyl--keto esters. The synthetic utility of the alkylated compounds is highlighted by the diastereoselective reduction and alkylation of the remaining ketone moiety to give various enantiomerically enriched congested 2,3-dihydroxycarboxylic acid esters.
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Catalytic Asymmetric Hydrophosphonylation of Ynones Invited
Uraguchi, Daisuke; Ito, Takaki; Nakamura, Shinji; Ooi, Takashi
Chemical Science Vol. 1 page： 488-490 2010
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Catalytic, highly enantioselective hydrophosphonylation of ynones has been achieved by exploiting the characteristic features of in situ generated chiral tetraaminophosphonium phosphite.
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Development of D2-Symmetric Chiral Tetraaminophosphonium Salts as a Catalyst for Asymmetric Phase-Transfer Reactions Invited Reviewed
Uraguchi, Daisuke; Ooi, Takashi
Vol. 39 page： 42-48 2010
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Development of Ion-Pair Cooperative Asymmetric Catalyses of Chiral Phosphonium Salts Possessing an Organic Anion Invited Reviewed
Ueki, Yusuke; Uraguchi, Daisuke; Ooi, Takashi
Vol. 52 page： 509-514 2010
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Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton Reviewed
Uraguchi, Daisuke; Kinoshita, Natsuko; Ooi, Takashi
J. Am. Chem. Soc. Vol. 132 page： 12240-12242 2010
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Chiral diaminodioxaphosphonium salts have been developed and their unique abilities as a chiral proton have been revealed through the establishment of a highly enantioselective protonation of α-amino acid-derived ketene disilyl acetals.
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Catalytic Asymmetric Direct Henry Reaction of Ynals: Short Syntheses of (2S,3R)-(+)-Xestoaminol C and (–)-Codonopsinines Reviewed
Uraguchi, Daisuke; Nakamura, Shinji; Ooi, Takashi
Angew. Chem. Int. Ed. Vol. 49 page： 7562–7565 2010
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Triple for all: Various optically active anti-β-nitro propargylic alcohols are synthesized by the catalytic stereoselective addition of nitroalkanes to ynals (the direct Henry reaction of ynals). The utilization of the rich chemistry of carbon–carbon triple bond allows rapid access to three natural products.
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Chiral Ammonium Betaines as an Ionic Nucleophilic Catalyst Reviewed
Uraguchi, Daisuke; Koshimoto, Kyohei; Miyake, Shuhei; Ooi, Takashi
Angew. Chem. Int. Ed. Vol. 49 page： 5567-5569 2010
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Catalyst debut: The chiral ammonium betaine 1 has been successfully applied to the asymmetric Steglich rearrangement as an ionic nucleophilic catalyst. The catalyzed reaction results in record levels of product enantioselectivity, and has a broad substrate scope. M.S.=molecular sieves, Troc=2,2,2-trichloroethoxycarbonyl.
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Performance of C1-symmetric chiral ammonium betaines as a catalyst for the enantioselective Mannich-type reaction of α-nitrocarboxylates Reviewed
Uraguchi, Daisuke; Koshimoto, Kyohei; Sanada, Chisato; Ooi, Takashi
Tetrahedron: Asymmetry Vol. 21 page： 1189-1190 2010
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Diastereo- and Enantioselective Direct Henry Reaction of Pyruvates Mediated by Chiral P-Spiro Tetraaminophosphonium salts Reviewed
Uraguchi, Daisuke; Ito, Takaki; Nakamura, Shinji; Sakaki, Sawako; Ooi, Takashi
Chem. Lett. Vol. 38 page： 1052-1053 2009.11
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The stereoselective direct Henry reaction of pyruvates mediated by chiral P-spiro tetraaminophosphonium salts is described. High levels of diastereo- and enantioselectivities have been achieved by the use of L-valine-derived (P,S)-2e bearing para-chlorophenyl groups as a precatalyst.
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*Chiral Organic Ion Pair Catalysts Assembled Through a Hydrogen-Bonding Network Reviewed
Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi
Science Vol. 326 page： 120-123 2009.10
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Research to develop structurally discrete, chiral supramolecular catalysts for asymmetric organic transformations has met with limited success. Here, we report that a chiral tetraaminophosphonium cation, two phenols, and a phenoxide anion appear to self-assemble into a catalytically active supramolecular architecture through intermolecular hydrogen bonding. The structure of the resulting molecular assembly was determined in the solid state by means of x-ray diffraction analysis. Furthermore, in solution the complex promotes a highly stereoselective conjugate addition of acyl anion equivalents to {alpha},β-unsaturated ester surrogates with a broad substrate scope. All structural components of the catalyst cooperatively participate in the stereocontrolling event.
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Chiral Arylaminophosphonium Barfates as a New Class of Charged Brønsted Acid for the Enantioselective Activation of Nonionic Lewis Bases Reviewed
Daisuke Uraguchi, Daisuke Nakashima and Takashi Ooi
J. Am. Chem. Soc. Vol. 131 ( 21 ) page： 7242-7243 2009.5
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Heterochiral [7.7]-P-spirocyclic arylaminophosphonium barfates have been designed as a novel charged, cationic Brønsted acid catalyst, and their catalytic and stereocontrolling abilities have been clearly demonstrated in the development of the unprecedented, highly enantioselective conjugate addition of arylamines to nitroolefins. This study uncovers a new function of chiral tetraaminophosphonium cations and its potential synthetic utility, thereby providing a new avenue to the molecular design of chiral charged Brønsted acid catalysts and their applications.
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Asymmetric Synthesis of α,α-Disubstituted-α-Amino Acids via Enantioselective Alkylation of Azlactones under Biphasic Conditions Using P-Spiro Chiral Tetraaminophosphonium Salts as a Phase-Transfer Catalyst Invited Reviewed
Uraguchi, Daisuke; Asai, Yoshihiro; Seto, Yuki; Ooi, Takashi
Synlett ( 4 ) page： 658-660 2009.2
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Highly enantioselective alkylation of azlactones derived from α-amino acids has been achieved under solid-liquid phase-transfer conditions using P-spiro chiral tetraaminophosphonium salt as a catalyst. The resulting alkylated azlactones can be readily converted into the corresponding α,α-disubstituted α-amino acids through simple acidic hydrolysis.
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Phase-Transfer-Catalyzed Enantioselective Alkylation of α-Benzoyloxy-β-Keto Ester Invited Reviewed
Takuya Hashimoto, Keigo Sasaki, Kazuhiro Fukumoto, Yuichi Murase, Takashi Ooi, Keiji Maruoka
Synlett ( 4 ) page： 661-663 2009.2
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Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive P-Nucleophile: Application to Asymmetric Hydrophosphonylation of Aldehydes Reviewed
Uraguchi, Daisuke; Ito, Takaki; Ooi, Takashi
J. Am. Chem. Soc. Vol. 131 ( 11 ) page： 3836–3837 2009.2
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The generation of chiral tetraaminophosphonium dialkyl phosphite has been detected by low-temperature NMR analysis, and its synthetic potential as a remarkably reactive P-nucleophile has been successfully demonstrated by its application to the establishment of highly efficient and enantioselective hydrophosphonylation of various aldehydes. A systematic evaluation of the organic-base-dependent generation of the requisite ion pair and its reactivity and selectivity as a P-nucleophile reveals that the structure of the cationic conjugate acid of the base is a key element both for substantial generation of phosphite anions with prominent nucleophilicity and for rigorous stereocontrol. This study provides not only experimental demonstration of the importance of the phosphite tautomer in the PC bond formation process but also a general yet valuable framework for the molecular design of even superior chiral organic base catalysts.
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*Site-directed Asymmetric Quaternization of a Peptide Backbone at C-Terminal Azlactone Reviewed
Uraguchi, Daisuke; Asai, Yoshihiro; Ooi, Takashi
Angew. Chem. Int. Ed. Vol. 48 ( 3 ) page： 733-737 2009.1
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Dual-purpose activation: Peptide C-terminal azlactones I undergo stereoselective alkylation with high efficiency by the use of a newly devised chiral tetraaminophosphonium salt as a phase-transfer catalyst (PTC), and the alkylated azlactone products II can be employed directly for peptide ligation (see scheme, LG=leaving group). In this way, a wide range of chiral quaternary -amino acid residues can be incorporated at specific sites of a peptide strand.
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Al Lewis acid-catalyzed regiodivergent 1,2-rearrangement of a-siloxy aldehydes: scope and mechanism Reviewed
Kohsuke Ohmatsu, Takayuki Tanaka, Takashi Ooi, Keiji Maruoka
Tetrahedron Vol. 65 page： 7516-7522 2009
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Regiodivergent 1,2-rearrangement of a-siloxy aldehydes bearing a-aryl and a-alkyl substituents into a-siloxy ketones has been realized by using different Al Lewis acid catalyst/solvent systems. The scope of this unprecedented protocol has been investigated with various substrates, clearly demonstrating its utility for the selective synthesis of two structural isomers from one substrate. Controlled experiments proved that the regiodivergency resulted from the switch of the migrating group.
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*Chiral Ammonium Betaines: A Bifunctional Organic Base Catalyst for Asymmetric Mannich-type Reaction of α-Nitrocarboxylates Reviewed
Uraguchi, Daisuke; Koshimoto, Kyohei; Ooi, Takashi
J. Am. Chem. Soc. Vol. 130 ( 33 ) page： 10878-10879 2008.7
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A chiral ammonium betaine, an intramolecular ion-pairing quaternary ammonium aryloxide, has been designed and its vast potential as an enantioselective organic base catalyst has been successfully demonstrated in the highly enantioselective direct Mannich-type reaction of α-substituted α-nitrocarboxylates with various N-Boc imines. The present study provides a conceptually new approach toward the design of bifunctional, chiral quaternary ammonium salts and their utilizations as a homogeneous organic molecular catalyst.
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Complete Switch of Migratory Aptitude in Aluminum-Catalyzed 1,2-Rearrangement of Differently α,α-Disubstituted α-Siloxy Aldehydes Reviewed
Ohmatsu, Kohsuke; Tanaka, Takayuki; Ooi, Takashi; Maruoka, Keiji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 47 ( 28 ) page： 5203-5206 2008.6
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Regiodivergent 1,2-rearrangement of alpha-siloxy aldehydes bearing alpha-aryl and alpha-alkyl substituents into alpha-siloxy ketones has been realized by using different Al Lewis acid catalyst/solvent systems. The scope of this unprecedented protocol has been investigated with various substrates, clearly demonstrating its utility for the selective synthesis of two structural isomers from one substrate.
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Synthesis of Chiral Tetraaminophosphonium Chlorides from N-BOC α-Amino Acid Esters Invited Reviewed
Uraguchi, Daisuke; Sakaki, Sawako; Ueki, Yusuke; Ito, Takaki; Ooi, Takashi
Heterocycles Vol. 76 page： 1081-1085 2008
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*Chiral Tetraaminophosphonium Carboxylate-Catalyzed Direct Mannich-Type Reaction Reviewed
Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi
J. Am. Chem. Soc. Vol. 130 page： 14088–14089 2008
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The cooperative asymmetric catalysis of chiral tetraaminophosphonium carboxylate (P,S)-1·OCOR has been established, and its synthetic utility has been successfully demonstrated by application to the highly enantioselective direct Mannich-type reaction of azlactones with N-sulfonyl imines. The present study stimulates the cultivation of the potential of the chiral quaternary onium salt catalysis by the structural modification of organic anion.
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光学活性な炭素の三角形を作る―Corey-Chaykovsky反応と親電子剤活性化法の組み合わせ Invited
浦口大輔、大井貴史
化学 Vol. 63 page： 66-67 2008
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Recent advances in asymmetric phase-transfer catalysis Reviewed
Ooi, Takashi; Maruoka, Keiji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 46 ( 23 ) page： 4222-4266 2007
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Development and Applications of C2-Symmetric, Chiral, Phase-Transfer Catalysts Invited Reviewed
Ooi, Takashi; Maruoka, Keiji
Aldrichimia Acta Vol. 40 page： 77-86 2007
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*Chiral Tetraaminophosphonium Salt-Mediated Asymmetric Direct Henry Reaction Reviewed
Uraguchi, Daisuke; Sakaki, Sawako; Ooi, Takashi
J. Am. Chem. Soc. Vol. 129 page： 12392-12393 2007
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A chiral tetraaminophosphonium salts possessing the phosphorus-centered [5.5]-spirocyclic core have been designed and synthesized in a single step from L-valine-derived diamine. The three-dimensional molecular structure was successfully verified by the single-crystal X-ray diffraction analysis, which also identified a secondary interaction between the phosphonium cation and chloride ion via double hydrogen-bonding. The potential of this novel onium salt as a chiral organic molecular catalyst has been demonstrated in an application to asymmetric direct Henry reaction.
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Design of chiral organocatalysts for practical asymmetric synthesis of amino acid derivatives Invited Reviewed
Maruoka, Keiji; Ooi, Takashi; Kano, Taichi
CHEMICAL COMMUNICATIONS ( 15 ) page： 1487-1495 2007
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Catalytic Asymmetric Rearrangement of α,α-Disubstituted α-Siloxy Aldehydes to Optically Active Acyloins Using Axially Chiral Organoaluminum Lewis Acids Reviewed
Ooi, Takashi; Ohmatsu, Kohsuke; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 129 page： 2410-2411 2007
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A catalytic asymmetric rearrangement of alpha,alpha-dialkyl-alpha-siloxy aldehydes has been developed based on the design of a stereochemically defined, axially chiral organoaluminum Lewis acid. The scope of this unprecedented stereoselective rearrangement has been investigated with representative substrates, in which impressive kinetic resolution of racemic, alpha,alpha-disubstituted alpha-siloxy aldehydes has also been achieved. These results clearly demonstrate the utility of the present approach for the catalytic enantioselective synthesis of various acyloins and tertiary alpha-hydroxy aldehydes not readily accessible by the previously known asymmetric methodologies.
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Advantage of in situ generation of N-arylsulfonyl imines from α-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction Reviewed
Ooi, Takashi; Uematsu, Yukitaka; Fujimoto, Jun; Fukumoto, Kazuhiro; Maruoka, Keiji
Tetrahedron Lett. Vol. 48 page： 1337-1340 2007
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Highly efficient, catalytic enantioselective synthesis of N-arylsulfonyl α-amino nitriles from the corresponding α-amido sulfones has been achieved under toluene–aqueous potassium cyanide biphasic conditions using chiral quaternary ammonium iodide (R,R,R)-1 as an effective phase-transfer catalyst. This Strecker synthesis involving the in situ generation of the reactive N-sulfonyl imines is advantageous for the cyanation of the substrates having primary and secondary alkyl substituents.
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Practical Stereoselective Synthesis of -Branched -Amino Acids through Efficient Kinetic Resolution in the Phase-Transfer-Catalyzed Asymmetric Alkylations Reviewed
Ooi, Takashi; Kato, Daisuke; Inamura, Koji; Ohmatsu, Kohsuke; Maruoka, Keiji
Org. Lett. Vol. 9 ( 20 ) page： 3945-3948 2007
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Phase-transfer-catalyzed alkylation of glycinate Schiff base with racemic secondary alkyl halides proceeded with excellent levels of syn- and enantioselectivities under the influence of chiral quaternary ammonium bromide 1d and 18-crown-6. The alkylation product can be selectively converted to the corresponding anti isomer, allowing the preparation of all the stereoisomers of -alkyl--amino acid derivatives, an extremely valuable chiral building block.
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Highly diastereo- and enantioselective formal conjugate addition of nitroalkanes to nitroalkenes by chiral ammonium bifluoride catalysis. Reviewed
Ooi, Takashi; Takada, Saki; Doda, Kanae; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 45 page： 7606-7608 2006
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An efficient catalysis of new chiral quaternary ammonium bifluoride in combination with silyl nitronates has been successfully utilized for achieving the highly diastereo- and enantioselective formal conjugate addition of nitroalkanes to nitroalkenes. This unique catalytic asymmetric protocol provides a reliable access to various 1,3-dinitro compounds bearing stereochemically defined two consecutive stereocenters, which serve as a versatile chiral building block in organic synthesis.
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Asymmetric phase-transfer catalysis of homo- and heterochiral quaternary ammonium salts: development and application of conformationally flexible chiral phase-transfer catalysts. Reviewed
Ooi, Takashi; Uematsu, Yukitaka; Kameda, Minoru; Maruoka, Keiji
Tetrahedron Vol. 62 page： 11425-11436 2006
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Inspired by the considerable difference of catalytic activity and stereocontrolling ability between the conformationally rigid, homo- and heterochiral quaternary ammonium bromides 1, conformationally flexible, N-spiro chiral quaternary ammonium bromides of type 4 have been designed and synthesized. Reliable procedures for the preparation of the appropriately substituted biphenyl subunits have been established by the repeated use of ortho magnesiation–halogenation as a key synthetic tool. The relationship between the structure of achiral biphenyl moiety and the reactivity and selectivity of 4 has been evaluated in the asymmetric alkylation of glycinate Schiff base 2 under typical phase-transfer conditions, leading to the identification of 4l as an optimal catalyst structure to exhibit an excellent enantiocontrol in the reactions with various alkyl halides. The molecular structure of 4l was determined by X-ray crystallographic analysis and its unique behavior in solution was examined by a variable-temperature 1H NMR study. These investigations uncovered that the observed high chiral efficiency originated from the efficient asymmetric phase-transfer catalysis of homochiral-4l, which rapidly equilibrated with heterochiral-4l of low catalytic activity and stereoselectivity.
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Asymmetric synthesis of α-acyl-γ-butyrolactones possessing all-carbon quaternary stereocenters by phase-transfer-catalyzed alkylation. Reviewed
Ooi, Takashi; Miki, Takashi; Fukumoto, Kazuhiro; Maruoka, Keiji
Adv. Synth. Catal. Vol. 348 page： 1539-1542 2006
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The enantioselective construction of all-carbon quaternary stereocenters on -acyl--butyrolactones has been achieved by the N-spiro chiral quaternary ammonium bromide 1-catalyzed alkylation under mild phase-transfer conditions. The resulting -alkylated keto lactones serve as valuable chiral building blocks in organic synthesis as clearly demonstrated by the facile conversion to optically active ,-dialkyl--amino acid derivatives via Schmidt rearrangement.
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Construction of Enantiomerically Enriched Tertiary α-Hydroxycarboxylic Acid Derivatives by Phase-Transfer-Catalyzed Asymmetric Alkylation of Diaryloxazolidin-2,4-diones Reviewed
Takashi, Ooi; Kazuhiro, Fukumoto; Keiji, Maruoka
Angew. Chem., Int. Ed. Vol. 45 page： 3839-3842 2006
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Catalytic, highly enantioselective alkylation of 3,5-diaryloxazoline-2,4-diones has been accomplished under mild phase-transfer conditions using designer chiral quaternary ammonium bromide as catalyst. This catalytic asymmetric glycolate alkylation procedure establishes chiral quaternary carbon centers, and provides a practical access to various optically active tertiary alpha-hydroxy-alpha-arylcarboxylic acid derivatives.
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Highly enantioselective monoalkylation of p-chlorobenzaldehyde imine of glycine tert-butyl ester under mild phase-transfer conditions.
Ooi, Takashi; Arimura, Yuichiro; Hiraiwa, Yukihiro; Yuan, Lin Ming; Kano, Taichi; Inoue, Toru; Matsumoto, Jun; Maruoka, Keiji
Tetrahedron: Asym. Vol. 17 page： 603-606 2006
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The selective monoalkylation of glycine tert-butyl ester aldimine Schiff base 3 has been realized in high chemical yield with excellent enantioselectivity under mild liquid–liquid phase-transfer conditions by the use of binaphthyl-derived chiral quaternary ammonium bromides 7 and 8 as catalysts. This achievement demonstrates that 3 can be used as a cost-effective substrate for the preparation of optically active α-alkyl-α-amino acid derivatives by chiral phase-transfer catalysis.
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Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase-Transfer Catalysis of Chiral Quaternary Ammonium Salts with a Tetranaphthyl Backbone. Reviewed
Ooi, Takashi; Uematsu, Yukitaka; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 128 page： 2548-2549 2006
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The phase-transfer-catalyzed, highly enantioselective cyanation of aldimines using aqueous KCN has been realized based on the molecular design of chiral quaternary ammonium iodide bearing a stereochemically defined tetranaphthyl backbone. A wide range of aliphatic aldimines, including those having -tert-alkyl substituents, is tolerated by the present system. This study represents a novel approach for the asymmetric Strecker-type reactions, which utilizes chiral phase-transfer catalysts for practical access to various unusual, optically pure -amino acids.
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Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected α-Amino Acid Amides toward Practical Asymmetric Synthesis of Vicinal Diamines, α-Amino Ketones, and α-Amino Alcohols. Reviewed
Ooi, Takashi; Takeuchi, Mifune; Kato, Daisuke; Uematsu, Yukitaka; Tayama, Eiji; Sakai, Daiki; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 127 page： 5073-5083 2005
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Highly enantioselective alkylation of protected glycine diphenylmethyl (Dpm) amide 1 and Weinreb amide 10 has been realized under phase-transfer conditions by the successful utilization of designer chiral quaternary ammonium salts of type 4 as catalyst. Particularly, remarkable reactivity of the chiral ammonium enolate derived from 1b and 4c allowed the reaction with less reactive simple secondary alkyl halides with high efficiency and enantioselectivity. An additional unique feature of this chiral ammonium enolate is its ability to recognize the chirality of -branched primary alkyl halides, which provides impressive levels of kinetic resolution and double stereodifferentiation during the alkylation, allowing for two - and -stereocenters to be controlled. Combined with the subsequent reduction using LiAlH4 in cyclopentyl methyl ether (CPME), this system offers a facile access to structurally diverse optically active vicinal diamines. Furthermore, the optically active -amino acid Weinreb amide 11 can be efficiently converted to the corresponding amino ketone by a simple treatment with Grignard reagents. In addition, reduction and alkylation of the optically active -amino ketone into both syn and anti -amino alcohols with almost complete relative and absolute stereochemical control have been achieved. With (S,S)- and (R,R)-4 in hand, the present approach renders both enantiomers of -amino amides including Weinreb amides readily available with enormous structural variation and also establishes a general and practical route to vicinal diamines, -amino ketones, and -amino alcohols with the desired stereochemistry.
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Asymmetric Michael Addition of Silyl Nitronates to Cyclic α,β-Unsaturated Ketones Catalyzed by Chiral Quaternary Ammonium Bifluorides: Isolation and Selective Functionalization of Enol Silyl Ethers of Optically Active γ-Nitro Ketones. Reviewed
Ooi, Takashi; Doda, Kanae; Takada, Saki; Maruoka, Keiji
Tetrahedron Lett. Vol. 47 page： 145-148 2005
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Highly enantioselective Michael addition of silyl nitronates to cyclic α,β-unsaturated ketones has been accomplished by the utilization of N-spiro C2-symmetric chiral quaternary ammonium bifluoride 1 as an efficient catalyst, offering a new route to the enol silyl ethers of optically active γ-nitro ketones. The synthetic utility of this transformation has been demonstrated by the diastereoselective derivatizations of the optically active enol silyl ethers to the corresponding α-substituted cyclic ketones having three consecutive stereochemically defined stereocenters.
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N-Spiro Chiral Quaternary Ammonium Bromide Catalyzed Diastereo- and Enantioselective Conjugate Addition of Nitroalkanes to Cyclic α,β-Unsaturated Ketones under Phase-Transfer Conditions. Reviewed
Ooi, Takashi; Takada, Saki; Fujioka, Shingo; Maruoka, Keiji
Org. Lett. Vol. 7 page： 5143-5146 2005
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Conjugate addition of various prochiral nitroalkanes to cyclic ,-unsaturated ketones was found to be efficiently catalyzed by N-spiro C2-symmetric chiral quaternary ammonium bromide 1b possessing a 3,5-bis(3,4,5-trifluorophenyl)phenyl substituent under solid-liquid phase-transfer conditions to afford the corresponding -nitro ketones in excellent chemical yields with unprecedented levels of diastereo- and enantiocontrol.
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Importance of Chiral Phase-Transfer Catalysts with Dual Functions in Obtaining High Enantioselectivity in the Michael Reaction of Malonates and Chalcone Derivatives. Reviewed
Ooi, Takashi; Ohara, Daisuke; Fukumoto, Kazuhiro; Maruoka, Keiji
Org. Lett. Vol. 7 page： 3195-3197 2005
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Highly enantioselective Michael addition of diethyl malonate to chalcone derivatives has been achieved under mild phase-transfer conditions by the successful utilization of N-spiro C2-symmetric chiral quaternary ammonium bromide 1 as a catalyst, which possesses diarylhydroxymethyl functionalities as a recognition site for the prochiral electrophile. This simple asymmetric Michael addition process was found to be quite effective for various chalcone derivatives, including those with heteroaromatic substituents.
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Dramatic Rate Enhancement of Asymmetric Phase-Transfer-Catalyzed Alkylations. Reviewed
Shirakawa, Seiji; Yamamoto, Kenichiro; Kitamura, Masanori; Ooi, Takashi; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 44 page： 625-628 2005
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Asymmetric Synthesis of Functionalized Aza-Cyclic Amino Acids with Quaternary Stereocenters by a Phase-Transfer-Catalyzed Alkylation Strategy. Reviewed
Ooi, Takashi; Miki, Takashi; Maruoka, Keiji
Org. Lett. Vol. 7 page： 191-193 2005
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Practical asymmetric synthesis of functionalized aza-cyclic -amino acid derivatives possessing quaternary stereocenters has been achieved by the phase-transfer-catalyzed alkylation of 2 or 3 using chiral quaternary ammonium bromide 1 as catalyst. Subsequent reduction and alkylation of the 3-keto carbonyl moiety of 4 proceeded with complete diastereochemical control to afford the corresponding -hydroxy aza-cyclic -amino acid derivatives having stereochemically defined consecutive quaternary carbon centers.
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Stereoselective Terminal Functionalization of Small Peptides for Catalytic Asymmetric Synthesis of Unnatural Peptides Reviewed
Maruoka, Keiji; Tayama, Eiji; Ooi, Takashi
Proc. Natl. Acad. Sci. USA Vol. 101 page： 5824-5829 2004
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The asymmetric phase-transfer catalytic alkylation of peptides has been achieved by the use of designed C2-symmetric chiral quaternary ammonium bromide 1 as catalyst. Excellent stereoselectivities were uniformly observed in the alkylation with a variety of alkyl halides and the efficiency of the transmission of stereochemical information was not affected by the side-chain structure of the preexisting amino acid residues. This method also enables an asymmetric construction of noncoded ,-dialkyl--amino acid residues at the peptide terminal. Since this chirality can be efficiently transferred to the adjacent amino acid moiety, our approach provides a general procedure not only for the highly stereoselective terminal functionalization of peptides but also for the sequential asymmetric construction of unnatural oligopeptides, which should play a vital role in the peptide-based drug discovery process.
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Elucidation and Synthetic Utility of the Double Electrophilic Activation Phenomenon. Reviewed
Ooi, Takashi; Takahashi, Makoto; Yamada, Masao; Tayama, Eiji; Omoto, Kiyoyuki; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 126 page： 1150-1160 2004
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A series of (2,7-disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) (2) has been readily prepared in situ by treatment of the requisite 2,7-disubstituted-1,8-biphenylenediol (1) with Me3Al (2 equiv) in CH2Cl2 at room temperature; this primarily relies on the successful establishment of a new synthetic procedure of 1 starting from inexpensive m-anisidine. Evaluation of 2 as a bidentate organoaluminum Lewis acid has been performed by the reduction of ketonic substrates using Bu3SnH as a hydride source in comparison to the conventional monodentate Lewis acid dimethylaluminum 2,6-xylenoxide (11), uncovering the significantly high activation ability of 2 toward carbonyl. Particularly, (2,7-dimethyl-1,8-biphenylenedioxy)bis(dimethylaluminum) (2a) exerted the highest reactivity, which has also been emphasized in the Mukaiyama aldol reaction. The structure of the bidentate Lewis acid 2 was unambiguously determined by single-crystal X-ray diffraction analysis of 2g possessing a bulky 3,5-di-tert-butylphenyl substituent, revealing the rigid dimeric assembly in the solid state. The double electrophilic activation of carbonyl substrate by 2a has been supported by low-temperature 13C NMR analysis as well as theoretical study using the Gaussian 98 program. Moreover, unique stereoselectivity has been observed in the 2a-promoted Mukaiyama Michael addition, and highly chemoselective functionalization of carbonyl compounds in the presence of their acetal counterparts has been realized using 2a. Finally, the effectiveness of 2a for the activation of ether functionality has been demonstrated in the Claisen rearrangement of allyl vinyl ethers.
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Meerwein-Ponndorf-Verley Alkynylation of Aldehydes: Essential Modification of Aluminum Alkoxides for Rate Acceleration and Asymmetric Synthesis. Reviewed
Ooi, Takashi; Miura, Tomoya; Ohmatsu, Kohsuke; Saito, Akira; Maruoka, Keiji
Org. Biomol. Chem. Vol. 2 page： 3312-3319 2004
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A novel carbonyl alkynylation has been accomplished based on utilization of the Meerwein–Ponndorf–Verley (MPV) reaction system. The success of the MPV alkynylation crucially depends on the discovery of the remarkable ligand acceleration effect of 2,2-biphenol. For example, the alkynylation of chloral (2c) with the aluminium alkoxide 6(R = Ph), prepared in situ from Me3Al, 2,2-biphenol and 2-methyl-4-phenyl-3-butyn-2-ol (1a) as an alkynyl source, proceeded smoothly in CH2Cl2 at room temperature to give the desired propargyl alcohol 3ca in almost quantitative yield after 5 h stirring. The characteristic feature of this new transformation involving no metal alkynides can be visualized by the fact that the alkynyl group bearing keto carbonyl was transferred successfully to aldehyde carbonyl without any side reactions on keto carbonyl. Although the use of (S)-1,1-bi-2-naphthol and its simple analogues was found to be unsuitable for inducing asymmetry in this reaction, design of new chiral biphenols bearing a certain flexibility of the biphenyl axis led to satisfactory results in terms of enantioselectivity as well as reactivity.
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「不斉有機触媒としてのキラル相間移動触媒-アミノ酸合成を中心として」 Invited
大井 貴史, 丸岡 啓二
化学と工業 Vol. 57 page： 711-715 2004
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「光学活性ジエン配位子が与える新しい不斉環境」
大井 貴史
page： 134 2004
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Asymmetric Organocatalysis of Structurally Well-Defined Chiral Quaternary Ammonium Fluorides. Reviewed
Ooi, Takashi; Maruoka, Keiji
Acc. Chem. Res. Vol. 37 page： 526-533 2004
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Organoaluminum-Mediated Selective 1,2-Rearrangement of γ,γ-Disubstituted γ-Amino α,β-Unsaturated Carbonyl Compounds Leading to Unsymmetrically Substituted Pyrroles. Reviewed
Ooi, Takashi; Ohmatsu, Kohsuke; Ishii, Hiroki; Saito, Akira; Maruoka, Keiji
Tetrahedron Lett. Vol. 45 page： 9315-9317 2004
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γ,γ-Dialkyl-γ-amino-α,β-unsaturated carbonyl compounds were found to undergo selective skeletal rearrangement under the influence of modified organoaluminum Lewis acid to give unsymmetrically substituted pyrroles through the rapid Paal–Knorr type cyclization upon acidic hydrolysis. This new structural reorganization of amino carbonyl compounds triggered by the 1,2-alkyl shift provides a unique entry to the synthesis of pyrroles, an important class of heterocycles with diverse biological activities.
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Anti-selective Asymmetric Synthesis of β-Hydroxy-α-Amino Acid Esters by the in Situ Generated Chiral Quaternary Ammonium Fluoride-Catalyzed Mukaiyama-Type Aldol Reaction. Reviewed
Ooi, Takashi; Taniguchi, Mika; Doda, Kanae; Maruoka, Keiji
Adv. Synth. Catal. Vol. 326 page： 1073-1076 2004
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The aldol coupling of ketene silyl acetal 2 derived from the glycinate Schiff base with aldehydes can be efficiently catalyzed by an in situ generated, chiral quaternary ammonium fluoride of type 1 under mild, neutral conditions, affording the corresponding anti--hydroxy--amino esters predominantly with excellent enantioselectivities.
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Evaluation of the Relationship Between the Catalyst Structure and Regio- as well as Stereoselectivity in the Chiral Ammonium Bifluoride-Catalyzed Asymmetric Addition of Silyl Nitronates to α,β-Unsaturated Aldehydes. Reviewed
Ooi, Takashi; Morimoto, Kumiko; Doda, Kanae; Maruoka, Keiji
Chem. Lett. Vol. 33 page： 824-825 2004
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Unique relationship between the catalyst structure and regio- and stereoselectivity in the chiral quaternary ammonium bifluoride–catalyzed asymmetric addition of silyl nitronates to α,β-unsaturated aldehydes has been reported.
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Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions. Reviewed
Ooi, Takashi; Kameda, Minoru; Fujii, Junichi; Maruoka, Keiji
Org. Lett. Vol. 6 page： 2397-2399 2004
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Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with -imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.
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Highly Enantioselective Alkylation of Glycine Methyl and Ethyl Ester Derivatives under Phase-Transfer Conditions: its Synthetic Advantage. Reviewed
Ooi, Takashi; Uematsu, Yukitaka; Maruoka, Keiji
Tetrahedron Lett. Vol. 45 page： 1675-1678 2004
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Phase-transfer alkylation of the benzophenone Schiff base of glycine methyl or ethyl ester (2) was found to be catalyzed by 3,4,5-F3-C6H2-NAS-Br [(S,S)-1] with high efficiency and excellent enantioselectivity. This procedure allows facile derivatization of the resulting alkylation products to other synthetically useful chiral building blocks.
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Design of New Chiral Phase-Transfer Catalysts with Dual Functions for Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones. Reviewed
Ooi, Takashi; Ohara, Daisuke; Tamura, Masazumi; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 126 page： 6844-6845 2004
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A new chiral ammonium bromide possessing diarylmethanol functionality as a substrate recognition site has been designed as a promising, dual-functioning catalyst for the highly enantioselective epoxidation of alpha,beta-unsaturated ketones under mild phase-transfer conditions. A variety of alpha,beta-unsaturated ketones can be epoxidized with rigorous stereochemical control, clearly demonstrating the effectiveness and utility of the present system. Further, a successful single-crystal X-ray diffraction analysis of the catalyst uncovered its distinctive three-dimensional molecular architecture and provided useful information for postulating the transition state.
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Efficient Asymmetric Catalysis of Chiral Organoaluminum Complex for Enantioselective Ene Reactions of Aldehydes. Reviewed
Ooi, Takashi; Ohmatsu, Kohsuke; Uraguchi, Daisuke; Maruoka, Keiji
Tetrahedron Lett. Vol. 45 page： 4481-4484 2004
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Chiral organoaluminum complex 1 efficiently catalyzed the asymmetric hetero-ene reaction of commercially available 2-methoxypropene (2) with aldehydes under mild conditions to give the corresponding β-hydroxymethyl ketones 3 in good to excellent chemical yields with high enantiomeric excesses. The asymmetric catalysis of 1 was further applied to the carbonyl addition of methallylsilanes, where exclusive formation of the optically active allylic silanes 5 was achieved.
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Development of Highly Diastereo- and Enantioselective Direct Asymmetric Aldol Reaction of a Glycinate Schiff Base with Aldehydes Catalyzed by Chiral Quaternary Ammonium Salts. Reviewed
Ooi, Takashi; Kameda, Minoru; Taniguchi, Mika; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 126 page： 9685-9694 2004
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A highly efficient direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes has been achieved under mild organic/aqueous biphasic conditions with excellent stereochemical control, using chiral quaternary ammonium salt 1b as a phase-transfer catalyst. The initially developed reaction conditions, using 2 equiv of aqueous base (1% NaOH (aq)), exhibited inexplicably limited general applicability in terms of aldehyde acceptors. The mechanistic investigation revealed the intervention of an unfavorable yet inevitable retro aldol process involving the chiral catalyst. On the basis of this information, a reliable procedure has been established by use of a catalytic amount of 1% NaOH (aq) and ammonium chloride, which tolerates a wide range of aldehydes to afford the corresponding anti--hydroxy--amino esters almost exclusively in an essentially optically pure form.
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Highly Enantioselective Conjugate Addition of Nitroalkanes to Alkylidenemalonates Using Efficient Phase-Transfer Catalysis of N-Spiro Chiral Ammonium Bromides. Reviewed
Ooi, Takashi; Fujioka, Shingo; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 126 page： 11790-11791 2004
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Highly enantioselective conjugate addition of nitroalkanes to alkylidenemalonates has been accomplished for the first time by the utilization of efficient phase-transfer catalysis of N-spiro C2-symmetric chiral quaternary ammonium bromide 1. For instance, simple mixing of nitropropane (2, R1 = Et), diisopropyl benzylidienemalonate (3, R2 = Ph), Cs2CO3 (1 equiv), and (S,S)-1 (1 mol %) in toluene at 0 C for 2.5 h gave rise to the desired conjugate addition product 4 (R1 = Et, R2 = Ph) quantitatively (anti/syn = 86:14) with 97% ee (anti isomer). The applicability of this procedure has been demonstrated with other representative alkylidenemalonates and nitroalkanes. Since 4 can be readily transformed into the corresponding -amino acid hydrochloride 5 without loss of diastereo- and enantioselectivity, the present method provides a new and practical access to various optically active -amino acid derivatives.
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Fluorotetraphenylbismuth: A New Reagent for Efficient Regioselective α-Phenylation of Carbonyl Compounds. Reviewed
Ooi, Takashi; Goto, Ryoji; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 125 page： 10494-10495 2003
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Synthesis and X-ray crystallographic characterization of fluorotetraphenylbismuth (1) has been achieved for the first time, revealing that the bismuth center of 1 adopts a distorted trigonal bipyramidal geometry with three ipso carbons at the equatorial sites and one ipso carbon and fluorine atom at the apical sites. Contrary to the previous common understanding of this type of organobismuth(V) compound, 1 was found to be thermally stable, maintaining its amphiphilic property. Hence, 1 can be used as an off-the-shelf reagent in organic synthesis, and its utility has been clearly demonstrated in applications to the efficient -phenylation of ketones and esters. For instance, simple mixing of 1 and 1-trimethylsiloxy-3,4-dihydronaphthalene in THF at -40 C and stirring at room temperature for 10 min gave rise to 2-phenyl-1-tetralone almost quantitatively without formation of the polyphenylated products. In addition to the generality of this method, applicability of our approach to the selective -alkenylation of carbonyl compounds was also demonstrated by the use of fluoro(2-phenylethenyl)tris(p-tolyl)bismuth (2) as a representative reagent. These results imply the vast potential of organobismuth(V) compounds of type 1 and 2 as useful precursors of a wide variety of pentavalent organobismuth compounds based on the utilization of the eminent fluorine-silicon interaction or the inherent basicity of the fluorine atom.
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Designer Chiral Quaternary Ammonium Bifluorides as an Efficient Catalyst for Asymmetric Nitroaldol Reaction of Silyl Nitronates with Aromatic Aldehydes. Reviewed
Ooi, Takashi; Doda, Kanae; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 125 page： 2054-2055 2003
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Designer chiral quaternary ammonium bifluoride 1 has been prepared, and both its catalytic and its chiral efficiency have been clearly demonstrated by achieving the first catalytic asymmetric nitroaldol reaction of silyl nitronate with aldehydes. For instance, the reaction of trimethylsilyl nitronate 2 (R1 = Me) with benzaldehyde (R2 = Ph) in THF in the presence of (S,S)-1 (2 mol %) proceeded smoothly at -78 C, giving the corresponding nitroaldol adduct 3 (R1 = Me, R2 = Ph) in 92% isolated yield (anti/syn = 92:8) with 95% ee (anti isomer). The method was found to be successfully applicable to other aromatic aldehydes and silyl nitronates, and a high level of anti selectivity and enantiomeric excess was constantly observed. This finding should lead to the further development of fluoride ion-catalyzed asymmetric carbon-carbon bond-forming reactions.
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Asymmetric Skeletal Rearrangement of Symmetrically α,α-Disubstituted α-Amino Aldehydes: A New Entry to Optically Active α-Hydroxy Ketones. Reviewed
Ooi, Takashi; Saito, Akira; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 125 page： 3220-3221 2003
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A unique asymmetric skeletal rearrangement of symmetrically ,-disubstituted -amino aldehydes has been accomplished for the first time using a chiral organoaluminum Lewis acid 1. For instance, treatment of (S)-2,2'-bis(trifluoromethanesulfonylamino)-1,1'-binaphthyl with Me3Al (1.0 equiv) in toluene at room temperature for 15 min and at 110 C for an additional 15 min produced (S)-1, and a subsequent reaction with -amino aldehyde 2a (R = CH2Ph) at -78 C for 4 h and at -40 C for 12 h resulted in the smooth rearrangement to the zwitterionic iminium intermediate A, which furnished the -hydroxy ketone 3a (R = CH2Ph) in 93% isolated yield with 95% ee (S) after acidic hydrolysis. This result, together with other representative examples, clearly demonstrates the effectiveness of the present method for the hitherto difficult asymmetric synthesis of acyloins. Furthermore, we found that the treatment of the in situ generated A with DIBAH afforded the corresponding anti amino alcohol exclusively without loss of enantiomeric excess. Our approach casts light on the previously unexplored yet potential utility of -amino aldehydes as synthetic building blocks and also provides a new entry to optically active -hydroxy ketones and 1,2-amino alcohols.
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Design of N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides as Novel Chiral Phase-Transfer Catalysts: Synthesis and Application to Practical Asymmetric Synthesis of α-Amino Acids. Reviewed
Ooi, Takashi; Kameda, Minoru; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 125 page： 5139-5151 2003
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A series of C2-symmetric chiral quaternary ammonium bromides 10 and 11 have been designed as a new, purely synthetic chiral phase-transfer catalyst, and readily prepared from commercially available optically pure 1,1'-bi-2-naphthol as a basic chiral unit. The details of the synthetic procedures of each requisite chiral binaphthyl subunit have been disclosed, and the structures of the assembled N-spiro chiral quaternary ammonium bromides 11a and 11f were unequivocally determined by single-crystal X-ray diffraction analysis. The reactivity and selectivity of these chiral ammonium bromides as chiral phase-transfer catalysts have been evaluated in the asymmetric alkylation of the benzophenone Schiff base of glycine ester 7 under mild liquid-liquid phase-transfer conditions, and the optimization of the reaction variables (solvent, base, and temperature) has also been conducted. Further, the scope and limitations of this asymmetric alkylation have been thoroughly investigated with a variety of alkyl halides, in which the advantage of the unique N-spiro structure of 11 and dramatic effect of the steric as well as the electronic properties of the aromatic substituents on the 3,3'-position of one binaphthyl moiety have been particularly emphasized. Finally, the potential synthetic utility of the present method for the practical asymmetric synthesis of structurally diverse natural and unnatural -amino acids has been demonstrated by its successful application to the facile asymmetric syntheses of (S)-N-acetylindoline-2-carboxylate, a key intermediate in the synthesis of the ACE inhibitor, and L-Dopa (L-3,4-dihydroxyphenylalanine) ester and its analogue.
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Highly Enantioselective Michael Addition of Silyl Nitronates to α,β-Unsaturated Aldehydes Catalyzed by Designer Chiral Ammonium Bifluorides: Efficient Access to Optically Active γ-Nitro Aldehydes and Their Enol Silyl Ethers. Reviewed
Ooi, Takashi; Doda, Kanae; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 125 page： 9022-9023 2003
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Highly enantioselective Michael addition of silyl nitronates to ,-unsaturated aldehydes has been accomplished by the utilization of designer N-spiro C2-symmetric chiral quaternary ammonium bifluoride 1 as an efficient catalyst, providing direct access to both optically active -nitro aldehydes, a very useful precursor to various complex organic molecules including aminocarbonyls, and their enol silyl ethers, a Mukaiyama donor of potential synthetic utility for further selective transformations. For instance, the reaction of trimethylsilyl nitronate 2 (R1 = Me) with trans-cinnamaldehyde (R2 = Ph, R3 = H) in toluene in the presence of (R,R)-1 (2 mol %) proceeded smoothly at -78 C to give the desired enol silyl ether 3 (R1 = Me, R2 = Ph, R3 = H) in 90% isolated yield (anti/syn = 83:17) with 97% ee (anti isomer), and simple treatment of 3 thus obtained with 1 N HCl in THF at 0 C afforded the corresponding -nitro aldehyde 4 quantitatively without loss of diastereo- and enantioselectivity.
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Highly Stereoselective N-Terminal Functionalization of Small Peptides by Chiral Phase-Transfer Catalysis. Reviewed
Ooi, Takashi; Tayama, Eiji; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 42 page： 579-582 2003
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Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis. Reviewed
Maruoka, Keiji; Ooi, Takashi
Chem. Rev. Vol. 103 page： 3013-3028 2003
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Enantioselective synthesis of α-amino acids by chiral phase-transfer catalysis. Reviewed
Ooi, Takashi; Maruoka, Keiji
Yuki Gosei Kagaku Kyokaishi Vol. 61 page： 1195 2003
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Practical Asymmetric Synthesis of Vicinal Diamines Through the Catalytic Highly Enantioselective Alkylation of Glycine Amide Derivatives. Reviewed
Ooi, Takashi; Sakai, Daiki; Takeuchi, Mifune; Tayama, Eiji; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 42 page： 5868-5870 2003
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A New N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromide Consisting of 4,6-Disubstituted Biphenyl Subunit as an Efficient Chiral Phase-Transfer Catalyst. Reviewed
Ooi, Takashi; Kubota, Yasushi; Maruoka, Keiji
Synlett page： 1931-1933 2003
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A new N-spiro chiral quaternary ammonium bromide has been designed and assembled from optically active 4,6-disubstitute­d biphenyl subunits. Its utility as an efficient chiral phase-transfer catalyst has been clearly demonstrated by application to the highly enantioselective alkylation of tert-butyl glycinate benzophenon­e Schiff base.
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Corrigendum:Highly Enantioselective Construction of Quaternary Stereocenters on β-Keto Esters by Phase-Transfer Catalytic Asymmetric Alkylation and Michael Reaction. Reviewed
Ooi, Takashi; Miki, Takashi; Taniguchi, Mika; Shiraishi, Misato; Takeuchi, Mifune; Maruoka, Keiji
Angew. Chem., Int.l Ed. Vol. 42 page： 3796-3798 2003
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A Scalable Synthesis of (R)-3,5-Dihydro-4H-dinaphth[2,1-c:1'2'-e]azepine. Reviewed
Ikunaka, Masaya; Maruoka, Keiji; Okuda, Yoshiaki; Ooi, Takashi
Org. Proc. Res. Dev. Vol. 7 page： 644-648 2003
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Environmentally benign scalable procedures are developed to supply enantiomerically pure (R)-3,5-dihydro-4H-dinaphth[2,1-c:1'2'-e]azepine 1 as its hydrogen oxalate salt in a five-step overall yield of 41%, which consist of the following: (1) bis O-triflation of (R)-1,1'-bi-2-naphthol 8 [(CF3SO2)2O, pyridine, PhMe; quantitative yield]; (2) Kumada's cross-coupling [MeMgI, NiCl2(dppp), tert-BuOMe; 96% yield]; (3) radical bromination [N-bromosuccinimide, 2,2'-azobisisobutyronitrile, cyclohexane; 54% yield]; (4) cyclization [allylamine, Et3N, THF, 86%]; (5) N-deallylation [1,3-dimethylbarbituric acid, Pd(OAc)2, Ph3P, PhMe] followed by crystalline salt formation with oxalic acid (overall 92% yield).
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New, Improved Procedure for the Synthesis of Structurally Diverse N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides. Reviewed
Ooi, Takashi; Uematsu, Yukitaka; Maruoka, Keiji
J. Org. Chem. Vol. 68 page： 4576-4578 2003
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Selective, direct ortho magnesiation of (S)-2,2'-bis(isopropoxycarbonyl)-1,1'-binaphthyl (6) has been achieved under mild conditions, using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2]. In combination with the subsequent reaction with the appropriate electrophiles, bromine and iodine, this method constitutes a key step in establishing a new and concise synthetic route to a wide variety of N-spiro C2-symmetric chiral quaternary ammonium bromides of type 1.
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Isopropoxyaluminum 1,1'-Biphenyl-2-oxy-2'-perfluorooctanesulfonamide as a Catalyst for Tishchenko Reaction. Reviewed
Ooi, Takashi; Ohmatsu, Kohsuke; Sasaki, Kouji; Miura, Tomoya; Maruoka, Keiji
Tetrahedron Lett. Vol. 44 page： 3191-3193 2003
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Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide (3) has been evaluated as an aluminum-based catalyst for the Tishchenko reaction. Compound 3 was found to exert high catalytic activity in the reaction with aliphatic aldehydes and also enabled smooth dimerization of enolizable aldehydes. This advantage was highlighted by the quantitative formation of ethyl acetate from acetaldehyde by the present system.
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Asymmetric Induction in the Neber Rearrangement of Simple Ketoxime Sulfonates under Phase-Transfer Conditions: Experimental Evidence for the Participation of an Anionic Pathway. Reviewed
Ooi, Takashi; Takahashi, Makoto; Doda, Kanae; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 124 page： 7640-7641 2002
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Phase-transfer catalysis has been successfully utilized for the Neber rearrangement of simple ketoxime sulfonates. For instance, treatment of (Z)-1a with p-toluenesulfonyl chloride (1.2 equiv), tetrabutylammonium bromide (5 mol %) and MeOH (10 equiv) in toluene-50% KOH aqueous solution (volume ratio = 3:1) at 0 C for 2 h, and subsequent benzoylation followed by acidic hydrolysis afforded the protected -amino ketone 2a in 80% isolated yield. On the basis of this finding, asymmetric Neber rearrangement with ketoxime (Z)-1a was examined under phase-transfer conditions using structurally rigid, C2-symmetric chiral quaternary ammonium bromide 3 as catalyst. The desired 2a was obtained in 80% yield and 51% ee. This represents the first experimental demonstration of the substantial involvement of anion pathway in the Neber rearrangement of simple ketoxime sulfonates. Importantly, the reaction with (E)-1a under otherwise similar conditions afforded racemic 2a in 61% yield. Moreover, enhanced enantioselectivity (63% ee) was observed in the rearrangement of the oxime sulfonate derived from (Z)-1b, and notably, use of mesitylene in place of toluene further increased the enantioselectivity to 70% ee. Our approach provides not only a new mechanistic insight but also an opportunity for extending the full synthetic utility of this classical yet useful rearrangement.
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Conformationally Flexible, Chiral Quaternary Ammonium Bromides for Asymmetric Phase-Transfer Catalysis. Reviewed
Ooi, Takashi; Uematsu, Yukitaka; Kameda, Minoru; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 41 page： 1551-1554 2002
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Practical Approach to the Meerwein-Ponndorf-Verley Reduction of Carbonyl Substrates with New Aluminum Catalysts. Reviewed
Ooi, Takashi; Ichikawa, Hayato; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 40 page： 3610-3612 2001
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"Amphiphilic" Cleavage of γ-Stannyl Ketones with ATPH/RLi: Application to Enone Fragmentation by the Conjugate Addition-Cleavage Sequence. Reviewed
Kondo, Yuichiro; Kon-i, Kana; Iwasaki, Atsuko; Ooi, Takashi; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 39 page： 414-416 2000
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「光学活性相間移動触媒が拓く有機合成−二相系での実用的不斉合成プロセス」 Invited
亀田 稔, 大井 貴史, 丸岡 啓二
化学 Vol. 55 page： 70-71 2000
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Chemistry of chelate-type hypervalent boron and aluminum. Utilization for selective organic synthesis. Reviewed
Uraguchi, Daisuke; Ooi, Takashi; Maruoka, Keiji
Yuki Gosei Kagaku Kyokaishi Vol. 58 page： 14-22 2000
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Practical Catalytic Enantioselective Synthesis of α,α-Dialkyl-α-amino Acids by Chiral Phase-Transfer Catalysis. Reviewed
Ooi, Takashi; Takeuchi, Mifune; Kameda, Minoru; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 122 page： 5228-5229 2000
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The Synthetic Utility of the Hypercoordination of Boron and Aluminum. Invited Reviewed
Maruoka, Keiji; Ooi, Takashi.
Chem. Eur. J. Vol. 5 page： 829-833 1999
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「ルイス酸・塩基を分子内にもつアルミニウム触媒−高度に制御された反応場をもつ不斉触媒の開発」 Invited
市川 隼人, 大井 貴史
化学 Vol. 54 page： 65-66 1999
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Pentacoordinate Organoaluminum Chemistry: Catalytic Efficiency of Me3Al in the Epoxide Cleavage with Alkynyllithiums. Reviewed
Ooi, Takashi; Kagoshima, Naoko; Ichikawa, Hayato; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 121 page： 3328-3333 1999
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Molecular Design of a C2-Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of α-Amino Acids. Reviewed
Ooi, Takashi; Kameda, Minoru; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 121 page： 6519-6520 1999
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High activation of carbonyl groups with bidentate Lewis acid catalysts. Reviewed
Ooi, Takashi; Asao, Naoki; Maruoka, Keiji
Yuki Gosei Kagaku Kyokaishi Vol. 56 page： 377-385 1998
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Synthesis of anticancer taxol using Lewis acid-type artificial enzyme. Invited
Maruoka, Keiji; Asao, Naoki; Ooi, Takashi
Ikagaku Oyo Kenkyu Zaidan Kenkyu Hokoku Vol. 16 page： 228-230 1998
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Exceptionally Bulky Lewis Acidic Reagent, MAD. Reviewed
Ooi, Takashi; Maruoka, Keiji
Rev. Heteroatom Chem. Vol. 18 page： 61-85 1998
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Rate acceleration in Nucleophilic Alkylation of Carbonyl Compounds with a New Template Containing Two Metallic Centers. Reviewed
Ooi, Takashi; Takahashi, Makoto; Maruoka, Keiji.
Angew. Chem., Int. Ed. Vol. 37 page： 835-837 1998
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Unprecedented Encapsulation of Carbonyl Guest with Designer Lewis Acid Receptor. Reviewed
Ooi, Takashi; Kondo, Yuichiro; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 37 page： 3039-3041 1998
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First Meerwein-Ponndorf-Verley Alkynylation: Nonorganometallic Way for Carbonyl Alkylations. Reviewed
Ooi, Takashi; Miura, Tomoya; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 120 page： 10790-10791 1998
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Hypercoordination of Boron and Aluminum: Synthetic Utility as Chelating Lewis Acids. Reviewed
Ooi, Takashi; Uraguchi, Daisuke; Kagoshima, Naoko; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 120 page： 5327-5328 1998
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「ルイス酸のデザイン-二点配位型システムの構築-」 Invited
大井 貴史
化学と工業 Vol. 50 page： 1496-1499 1997
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Fluorine-Assisted Selective Alkylation to Fluorinated Epoxides and Carbonyl Compounds: Implication of Pentacoordinate Trialkylaluminum Complexes. Reviewed
Ooi, Takashi; Kagoshima, Naoko; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 119 page： 5754-5755 1997
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Highly Efficient, Catalytic Meerwein-Ponndorf-Verley Reduction with a Novel Bidentate Aluminum Catalyst. Reviewed
Ooi, Takashi; Miura, Tomoya; Maruoka, Keiji
Angew. Chem., Int. Ed. Vol. 37 page： 2347-2349 1997
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Conjugate Allylation to α,β-Unsaturated Aldehydes with the New Chemzyme p-F-ATPH. Reviewed
Ooi, Takashi; Kondo, Yuichiro; Maruoka, Keiji.
Angew. Chem., Int. Ed. Engl. Vol. 36 page： 1183-1185 1997
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Remarkable Template Effect of a Lewis Acidic Receptor in Intramolecular Radical Cyclizations. Reviewed
Ooi, Takashi; Hokke, Yasutoshi; Maruoka, Keiji
Angew. Chem., Int. Ed. Engl. Vol. 36 page： 1181-1183 1997
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Exceptionally bulky Lewis acidic reagent, MAD. Reviewed
Ooi, Takashi; Maruoka, Keiji
Yuki Gosei Kagaku Kyokaishi Vol. 54 page： 200-211 1996
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(2,7-Dimethyl-1,8-biphenylenedioxy)bis(dimethylaluminum) as a Bidentate Lewis Acid: Its Reactivity and Selectivity in Organic Synthesis. Reviewed
Ooi, Takashi; Takahashi, Makoto; Maruoka, Keiji
J. Am. Chem. Soc. Vol. 118 page： 11307-11308 1996
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Rearrangement of trans-stilbene oxide to diphenylacetaldehyde with catalytic methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (oxirane, 2,3-diphenyl-, trans- to benzeneacetaldehyde, α-phenyl-). Reviewed
Ooi, Takashi; Maruoka, Keiji; Yamamoto, Hisashi
Organic Syntheses Vol. 72 page： 95-103 1995
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「自己複製する人工分子」 Invited
大井 貴史
ファルマシア Vol. 31 page： 1034-1035 1995
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Asymmetric Diels-Alder Reaction of Unsymmetrical Maleates. A Chemical Access to Chiral, Unsymmetrical cis-Cyclohexene-1,2-dicarboxylates. Reviewed
Maruoka, Keiji; Akakura, Matsujiro; Saito, Susumu; Ooi, Takashi; Yamamoto, Hisashi
J. Am. Chem. Soc. Vol. 116 page： 6153-6158 1994
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「エポキシドの選択的転位を機軸とする不斉アルドール合成」 Invited
大井 貴史, 丸岡 啓二, 山本 尚
化学 Vol. 48 page： 218-219 1993
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Unprecedented Stereochemical Control in the Organoaluminum-Promoted Intramolecular Ene Reactions of δ,ε-Unsaturated Aldehydes. Reviewed
Maruoka, Keiji; Ooi, Takashi; Yamamoto, Hisashi
J. Am. Chem. Soc. Vol. 112 page： 9011-9012 1990
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Organoaluminum-Promoted Rearrangement of Epoxy Silyl Ethers to β-Siloxy Aldehydes. Reviewed
Maruoka, Keiji; Ooi, Takashi; Yamamoto, Hisashi
J. Am. Chem. Soc. Vol. 111 page： 6431-6432 1989
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Books
Books 27
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Supramolecular Catalysis: New Directions and Developments Reviewed
Kohsuke Ohmatsu, Daisuke Uraguchi, Takashi Ooi（ Role： Contributor , Assembled Ionic Molecular Catalysts and Ligands）
Wiley‐VCH 2022.1
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Total pages：614 Responsible for pages：41-53 Language：English Book type：Scholarly book
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Anion-Binding Catalysis Reviewed
Kohsuke Ohmatsu,Takashi Ooi（ Role： Contributor , 1,2,3-Triazoles and 1,2,3-Triazolium Ions as Catalysts）
Wiley-VCH 2021.3
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Organic Molecular Catalysts in Radical Chemistry: Challenges Toward Selective Transformations
Daisuke Uraguchi, Kohsuke Ohmatsu, Takashi Ooi（ Role： Joint author）
2019
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多機能型キラルオニウム塩の設計に基づく高選択的分子変換
大松 亨介, 浦口 大輔, 大井 貴史（ Role： Joint author）
シーエムシー出版 2018
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Language：Japanese Book type：Scholarly book
有機分子触媒の開発と工業利用
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Site-Selective Conjugate Addition through Catalytic Generation of Ion-Pairing Intermediates
（ Role： Joint author）
2016
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イオン対を中心とした不斉塩基触媒
浦口 大輔, 大井 貴史（ Role： Joint author）
日本化学会 2016
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Asymmetric phase-transfer catalysis
（ Role： Joint author）
2013
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Language：English Book type：Scholarly book
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イオン性キラル触媒～新しい分子設計へのこだわり～
大松 亨介, 大井 貴史（ Role： Joint author）
日本化学会 2013
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CSJカレントレビュー「キラル化学：その起源から最新のキラル材料研究まで」八島栄次
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Axially Chiral C2-Symmetric Catalysts
（ Role： Joint author）
2013
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Hydrogen-Bonding Catalysts Other than Ureas and Thioureas
（ Role： Joint author）
2012
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6.1 C-C Bond Formation: Alkylation
（ Role： Joint author）
2012
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ACS Symposium Series (2009), 1009(Asymmetric Synthesis and Application of .alpha.-Amino Acids)
Takashi Ooi（ Role： Sole author）
ACS publications 2009
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“Asymmetric Phase Transfer Catalysis” K. Maruoka Ed. Chapter:“Cinchona-derived chiral phase-transfer catalysts for amino acid synthesis”
Ooi Takashi（ Role： Sole author）
Wiley-VCH 2008
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“Asymmetric Phase Transfer Catalysis” K. Maruoka Ed. Chapter:“Cinchona-derived chiral phase-transfer catalysts for amino acid synthesis”
Shirakawa, Seiji; Ooi, Takashi; Maruoka, Keiji（ Role： Joint author）
Wiley-VCH 2008
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“Enantioselective Organocatalysis: Reactions and Experimental Procedures ” P. I. Dalko Ed.Chapter:“Ammonium Ions as Chiral Templates”
T. Ooi, K. Maruoka（ Role： Joint author）
Wiley 2007
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Language：English
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“Asymmetric Synthesis - The Essentials ” M. Christmann, S. Bräse Eds.Chapter:“Chiral Carbonyl Lewis Acid Complexes in Asymmetric Syntheses”
K. Maruoka, T. Ooi（ Role： Joint author）
VCH 2007
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Language：English
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"Quaternary Stereocenters" J. Christoffers and A. Baro Eds.; chap: Phase-Transfer Catalysis
T. Ooi, K. Maruoka（ Role： Joint author）
Wiley-VCH 2005
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Language：English
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"Science of Synthesis Houben-Weyl Method of Molecular Transformations, Compounds of Groups 13 and 2" H. Yamamoto Ed.; chap: Aluminum Alkoxides, Phenoxides, Thiolates, Selenolates and Amides”
T. Ooi, K. Maruoka（ Role： Joint author）
Springer 2004
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Language：English
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「有機合成のための触媒反応103」 檜山爲次郎・野崎京子編， 光学活性相間移動触媒を用いるグリシンの不斉アルキル化
大井 貴史, 丸岡 啓二（ Role： Joint author）
2004
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Language：Japanese
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「化学便覧 基礎編 第６版」日本化学会編， 官能基変換反応 （オレフィン類の異性化反応、エポキシド類の開環反応、エステル類やアミド類の加水分解反応及び加アルコール分解反応）
大井 貴史, 丸岡 啓二（ Role： Joint author）
2004
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Language：Japanese
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「実験化学講座 第５版 有機化合物の合成Ⅵ」 村上正浩編，第2章5 有機アルミニウム化合物を用いる合成反応
大井 貴史, 丸岡 啓二（ Role： Joint author）
丸善株式会社 2004
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Language：Japanese
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「有機金属反応剤ハンドブック」 玉尾皓平編著， アルミニウム（Al）
丸岡 啓二, 大井 貴史（ Role： Joint author）
化学同人 2003
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Language：Japanese
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“My Favorite Organic Synthesis”The Society of Synthetic Organic Chemistry, Japan Ed.; chap: Design of Artificial Acid and Base Catalysts for Selective Organic Synthesis
K. Maruoka, T. Ooi（ Role： Joint author）
Kagaku-Dojin Publishing Co. 2002
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Language：Japanese
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“Lewis Acids in Organic Synthesis”, chap: Achiral Al(III) Lewis Acids
T. Ooi, K. Maruoka（ Role： Joint author）
Wiley-VCH 2000
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Language：English
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“Modern Carbonyl Chemistry” J. Otera Ed.; chap: Carbonyl-Lewis Acid Complexes
T. Ooi, K. Maruoka（ Role： Joint author）
Wiley-VCH 2000
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Language：English
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“Comprehensive Asymmetric Catalysis” E. N. Jacobsen, A. Pfaltz and H. Yamamoto Eds.; chap: Hetero-Diels-Alder and Related Reactions
T. Ooi, K. Maruoka（ Role： Joint author）
Springer 1999
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Language：English
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「有機化学 基礎の基礎 100のコンセプト」 山本嘉則編著，「コンセプト 10-19」
大井 貴史, 丸岡 啓二（ Role： Joint author）
化学同人 1997
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Language：Japanese
MISC
MISC 8
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Catalytic acceptorless dehydrogenative coupling mediated by photoinduced hydrogen-atom transfer Invited Reviewed
Kohsuke Ohmatsu, Takashi Ooi
Nature Synthesis Vol. 2 page： 209 - 216 2023.1
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Authorship：Corresponding author Language：English Publishing type：Article, review, commentary, editorial, etc. (scientific journal)
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Catalysis of chiral iminophosphorane for simultaneous control of multiple selectivity: experimental and theoretical investigation Reviewed
2021.5
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Cationic Organic Catalysts or Ligands in Concert with Metal Reviewed
Kohsuke Ohmatsu,Takashi Ooi
Topics in Current Chemistry 2019.10
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Chemistry of Ammonium Betaines: Application to Ion-Pair Catalysis for Selective Organic Transformations Reviewed
Journal of Synthetic Organic Chemistry, Japan 2018.11
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Development of Ion-Paired Chiral Ligands for Asymmetric Transition-Metal Catalysis Reviewed
2015.3
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Design of supramolecular chiral ligands for asymmetric metal catalysis Reviewed
Kohsuke Ohmatsu, Takashi Ooi
Tetrahedron Letters 2015.3
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Recent Advances in Asymmetric Phase-Transfer Catalysis Reviewed
Takashi Ooi, Keiji Maruoka
Angewandte Chemie 2007.5
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Design of Chiral Organocatalysts for Practical Asymmetric Synthesis of Amino Acid Derivatives Reviewed
Keiji Maruoka, Takashi Ooi and Taichi Kanoa
Chemical Communications 2006.12
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DOI： http10.1039/b613049f
Presentations
Presentations 62
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Toward Catalytic Control of Photoinduced Radical Reactions Invited International conference
Takashi Ooi
Stereochemisty Gordon Research Conference 2024.7.22 Gordon Research Conference
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Event date： 2024.7
Language：English Presentation type：Oral presentation (invited, special)
Venue：Salve Regina University, Rhode Island Country：United States
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Development of Multifunctional Organic Photocatalysts Invited International conference
Takashi Ooi
1st Maruoka Conference at GDUT on the Frontier of Organic Synthesis and Catalysis 2025.1.17 GDUT
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Event date： 2025.1
Language：English Presentation type：Oral presentation (invited, special)
Venue：GDUT, Guangzhou Country：China
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光駆動ラジカル反応の触媒的な制御 Invited
2024.10.24
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Event date： 2024.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Development of Multifunctional Photocatalysts Invited International conference
Takashi Ooi
8th UK-Japan Catalysis Meeting 2024.9.26 Green Catalysis Science
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Event date： 2024.9
Language：English Presentation type：Oral presentation (invited, special)
Venue：Kyoto University Country：Japan
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光駆動ラジカル反応の触媒的な制御 Invited
2024.9.20
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Event date： 2024.9
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Toward Catalytic Control of Photoinduced Radical Reactions Invited International conference
Takashi Ooi
2024 International IRTG-IRCCS-ILR Symposium 2024.5.7 IRTG-IRCCS-ILR
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Event date： 2024.5
Language：English Presentation type：Oral presentation (invited, special)
Venue：Münster Country：Germany
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Organic Zwitterions for Hydrogen Atom Transfer Catalysis Invited International conference
Takashi Ooi
International Symposium on Catalysis and Fine Chemicals (C&FC) 2023 2023.12.6
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Event date： 2023.12
Language：English Presentation type：Oral presentation (invited, special)
Venue：Tokyo
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Exploiting Zwitterions for Catalyst and Reaction Development Invited International conference
Takashi Ooi
3rd Japanese-Spanish Symposium on Organic Synthesis (3rd JSSOS) 2023.10.17
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Event date： 2023.10
Language：English Presentation type：Oral presentation (invited, special)
Venue：Donostia/San Sebastián, Spain
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Exploiting Zwitterions for Catalyst and Reaction Development Invited International conference
Takashi Ooi
CRC 325 Assembly Controlled Chemical Photocatalysis, International Conference on Light Induced Transformations: LIT 2023 2023.10.4
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Event date： 2023.10
Language：English Presentation type：Oral presentation (invited, special)
Venue：Regensburg, Germany
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Exploiting Organic Zwitterions for Catalyst and Reaction Development Invited International conference
Takashi Ooi
The 6th ICReDD International Symposium & 3rd Akira Suzuki Awards Ceremony 2023.9.10
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Event date： 2023.9
Language：English Presentation type：Oral presentation (invited, special)
Venue：Sapporo
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イオン対を鍵とする合成化学 Invited
大井 貴史
日本プロセス化学会 2023 サマーシンポジウム 2023.8.3
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Event date： 2023.8
Language：Japanese Presentation type：Oral presentation (invited, special)
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Exploiting Zwitterions in Organic Synthesis and Catalysis Invited International conference
Takashi Ooi
27th International Symposium: Synthesis in Organic Chemistry 2023.7.27
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Event date： 2023.7
Language：English Presentation type：Oral presentation (invited, special)
Venue：Oxford, UK
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光駆動ラジカル反応の触媒的制御 Invited
大井 貴史
第33回万有福岡シンポジウム：エクセレント有機分子の設計、合成、応用 2023.6.3
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Event date： 2023.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：福岡
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Organic Zwitterions for Hydrogen Atom Transfer Catalysis Invited International conference
Takashi Ooi
7th UK-Japan Catalysis Meeting Contemporary Catalysis for a Sustainable World 2023.4.17
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Event date： 2023.4
Language：English Presentation type：Oral presentation (general)
Venue：Oxford, UK
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Asymmetric Catalysis of Designer Chiral Organic Ion Pairs Invited International conference
Takashi Ooi
Chemical Science symposium 2022: Sustainable synthesis and catalysis 2022.11.11 The Royal Society of Chemistry
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Event date： 2022.11
Language：English Presentation type：Oral presentation (keynote)
Venue：London Country：United Kingdom
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Behavior of Molecules: From Catalysis to Biological Functions Invited International conference
Takashi Ooi
Department Lecture, CSIR-Central Drug Research Institute 2022.10.21 CSIR-Central Drug Research Institute
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Event date： 2022.10
Language：English Presentation type：Oral presentation (invited, special)
Venue：On-line
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Hybrid Catalysis with Zwitterionic 1,2,3-Triazolium Amidates International conference
大井 貴史
The 3rd International Symposium on Hybrid Catalysis for Enabling Molecular Synthesis on Demand 2022.6.30
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Event date： 2022.6 - 2022.7
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Non-nucleophilic Chiral Borate Ions for Catalytic Control of Cationic Reactive Intermediates Invited International conference
大井 貴史
2021.12.22
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Event date： 2021.12
Language：English Presentation type：Oral presentation (keynote)
Country：India
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Hybrid Catalysis for Stereocontrol in Photoinduced Radical Reactions Invited International conference
Hybrid Catalysis (#358), The International Chemical Congress of Pacific Basin Societies 2021.12.19
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Event date： 2021.12
Language：English Presentation type：Oral presentation (invited, special)
Venue：virtual-on line
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Asymmetric Catalysis of Designer Chiral Organic Ion Pairs Invited International conference
New Aspects on Organocatalysts (#379), The International Chemical Congress of Pacific Basin Societies 2021 2021.12.21
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Event date： 2021.12
Language：English Presentation type：Oral presentation (invited, special)
Venue：virtual-on line
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体内にもある単純な有機分子が触媒になる Invited
大井 貴史
ノーベル賞特別講演会「気候変動と有機触媒」 2021.11.20
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Event date： 2021.11
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン（名古屋大学） Country：Japan
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分子を創り、振舞いを理解する：触媒機能から生物活性まで Invited
大井 貴史
有機合成化学協会中国四国支部「有機合成ミニシンポジウム2021」 2021.5.22 有機合成化学協会中国四国支部
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Event date： 2021.5
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン（岡山大学） Country：Japan
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有機イオン対の分子設計に基づく触媒機能の創出 Invited
大井貴史
日本化学会第101春季年会(2021) 2021.3.21 日本化学会
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Event date： 2021.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン
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ないものを創る希望の有機触媒 Invited
大井貴史
第10回CSJ化学フェスタ2020 2020.10.22 日本化学会
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Event date： 2020.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン
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分子を創り、振舞いを理解する Invited
大井貴史
第31回万有仙台シンポジウム 2020.10.17 公益財団法人 MSD生命科学財団
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Event date： 2020.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン
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Behavior of Molecules: From Catalysis to Biological Functions Invited
Takashi Ooi
CBC Virtual Seminar Series, Nanyang Technological University 2020.6.12 Division of Chemistry and Biological Chemistry, Nanyang Technological University
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Event date： 2020.6
Language：English Presentation type：Oral presentation (invited, special)
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Molecular Design and Synthetic Applications of Chiral 1,2,3-Triazolium Salts International conference
Takashi Ooi
Gordon Research Conference on Heterocyclic Compounds
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Event date： 2011.6 - 2011.7
Language：English Presentation type：Oral presentation (invited, special)
Country：United States
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キラル第四級オニウム塩の分子設計から生まれる触媒機能
大井 貴史
平成23年度前期 （春季）有機合成化学講習会「わが国の有機合成の底力」
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Event date： 2011.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：長井記念ホール、東京 Country：Japan
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Design and Applications of Chiral Quaternary Onium Salts Featuring Anion -Recognition Ability International conference
Takashi Ooi
The XII Spring Meeting of the Division of Synthetic C hemistry
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Event date： 2011.6
Language：English Presentation type：Oral presentation (invited, special)
Country：Finland
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Molecular Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses International conference
Takashi Ooi
Syngenta Lecture
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Event date： 2011.4
Language：English Presentation type：Oral presentation (invited, special)
Country：Switzerland
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Molecular Design and Synthetic Applications of Chiral Quaternary Oniums Featuring Anion-Recognition Ability International conference
Takashi Ooi
Lecture at University of Basel
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Event date： 2011.4
Language：English Presentation type：Oral presentation (invited, special)
Country：Switzerland
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Design and Synthetic Application of Chiral 1,2,3-Triazoliums as Cationic Organic Catalysts with Anion-Recognition Ability International conference
Takashi Ooi
3rd UK/Japan Symposium on Catalytic Asymmetric Synthesis
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Event date： 2011.4
Language：English Presentation type：Oral presentation (invited, special)
Country：United Kingdom
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自然に組み上がる触媒：その働きを操る
大井貴史
文部科学省科学研究費 特定領域研究「協奏機能触媒」（終了研究領域）講演会「私たちに役立つ触媒って何？」
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Event date： 2011.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：東工大蔵前会館 Country：Japan
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Chiral Ammonium Betaines as a Unique Organic Molecular Catalyst International conference
The 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
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Event date： 2010.12
Language：English Presentation type：Oral presentation (invited, special)
Country：United States
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有機イオン対の構造制御に基づく触媒機能創出と応用
大井貴史
第3回有機触媒シンポジウム
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Event date： 2010.9
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Unique Asymmetric Catalysis of Supramolecularly Assembled Chiral Tetraaminophosphonium Phenoxides International conference
International Symposium on Organocatalysis Muelheim an der Ruhr ISOμ 2010
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Event date： 2010.7
Language：English Presentation type：Oral presentation (invited, special)
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Molecular Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses International conference
The International Symposia on Advancing the Chemical Sciences 1st (ISACS1), Challenges in Organic Chemistry and Chemical Biology
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Event date： 2010.7
Language：English Presentation type：Oral presentation (invited, special)
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アミノホスホニウム塩の分子設計に基づく酸・塩基触媒機能の創出と応用
大井 貴史
日本薬学会第130年会 一般シンポジウム「有機触媒研究の新展開」
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Event date： 2010.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses
The 4th International Symposium for Young Elements Chemists2009 Workshop on Organometallic Chemistry
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Event date： 2009.10
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Molecular Design and Synthetic Applications of Chiral Tetraaminophosphonium Salts
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Event date： 2009.10
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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アミノホスホニウム塩の分子設計に基づく触媒機能創出と応用
大井貴史
理研シンポジウム 第４回 「有機合成化学のフロンティア」
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Event date： 2009.7
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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機能性イオン対協奏作用型有機分子触媒系の構築と応用
大井貴史
文部科学省科学研究費補助金特定領域研究「協奏機能触媒」第６回公開シンポジウム
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Event date： 2009.4
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Toward Asymmetric Synthesis of Oligopeptides Site-Specifically Incorporating Chiral α,α-Dialkyl-α-Amino Acid Residues
UK/Japan Symposium on Asymmetric Catalysis
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Event date： 2008.12
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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新規基質認識型キラル有機強塩基触媒の創製と応用
大井 貴史
文部科学省科学研究費補助金特定領域研究「炭素資源の高度分子変換」第６回公開シンポジウム
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Event date： 2008.12
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Molecular Design and Synthetic Utilities of Chiral Organic Ion Pair Catalysts International conference
5th Annual Japanese-German Frontiers of Science Symposium
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Event date： 2008.10
Language：English Presentation type：Oral presentation (invited, special)
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Chiral Ammonium Betaines: Design and Application as an Enantioselective Orgainc Base Catalyst International conference
3rd International Conference on Cutting-Edge Organic Chemistry in Asia under Asian Core Program (ICCEOA-3)
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Event date： 2008.10
Language：English Presentation type：Oral presentation (invited, special)
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アミノホスホニウム塩の分子設計に基づく触媒機能創出と不斉合成への活用
大井 貴史
北海道大学グローバルCOEシンポジウム「触媒的不斉合成の最先端」
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Event date： 2008.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Molecular Design and Synthetic Applications of Chiral Tetraaminophosphonium Salts International conference
1st Japan-Singapore Bilateral Symposium on Catalysis
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Event date： 2008.1
Language：English Presentation type：Oral presentation (invited, special)
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Molecular Design and Synthetic Applications of Chiral Tetraaminophosphonium Salts
4th Japanese-Sino Symposium on Organic Chemistry for Young Scientists
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Event date： 2007.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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「キラルオニウム塩の分子設計に基づく触媒的不斉合成」
2007年度ファインケミカルズ合成触媒研究会シンポジウム
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Event date： 2007.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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「キラルオニウム塩の分子設計に基づく実践的不斉合成」
有機合成化学協会九州山口支部 平成20年度 有機合成化学講演会「合成有機化学のフロンティア」
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Event date： 2007.5
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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"Development of Phase-Transfer-Catalyzed Asymmetric Strecker Reaction Based on the Molecular Design of Chiral Quaternary Ammonium Salts" International conference
American Chemical Society 233rd National Meeting
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Event date： 2007.3
Language：English Presentation type：Oral presentation (invited, special)
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「相間移動触媒作用を活かした実用的不斉合成」
近畿化学協会有機金属部会平成18年度第4回例会
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Event date： 2007.2
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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キラルアンモニウム塩の分子設計に基づく二相系での不斉ストレッカ－反応の開発
名古屋大学 21 世紀 COE プログラム「物質科学の拠点形成：分子機能の解明と創造」第３回 有機化学若手研究会
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Event date： 2006.12
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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「不斉炭素－炭素結合形成」
実力養成化学スクール：第４回「キラル化学－不斉合成」研修コース
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Event date： 2006.8
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Selective Structural Reorganization of Amino Carbonyl Compounds through Organoaluminum-Mediated 1,2-Rearrangement International conference
The 2005 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2005)
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Event date： 2005.12
Language：English Presentation type：Oral presentation (invited, special)
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キラルアンモニウム塩の分子設計を基盤とする実用的不斉合成プロセスの開拓
北海道大学触媒化学研究センター研究討論会「明日を創る有機化学」
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Event date： 2004.11
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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光学活性アンモニウムビフルオリドのデザインを機軸とする触媒的不斉合成
有機フッ素化学セミナー「含フッ素リガンドの展開」
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Event date： 2004.8
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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N-スピロ型光学活性相間移動触媒の創製と実用的アミノ酸合成への応用
21COE京都大学化学連携研究教育拠点「有機元素化学セミナー」
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Event date： 2004.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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二点配位型アルミニウム触媒の創製と精密合成への応用
特定領域研究「集積型金属錯体」主催「錯体化学の未来シンポジウム」
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Event date： 2000.2
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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精密分子認識を指向した二点配位型ルイス酸の創製と応用
日本化学会第76春季年会
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Event date： 1999.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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二点配位型アルミニウム反応剤の創製と合成化学的展開
有機合成化学協会東北北海道支部主催「若手研究者のための有機化学札幌セミナー」
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Event date： 1998.7
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
Research Project for Joint Research, Competitive Funding, etc.
Research Project for Joint Research, Competitive Funding, etc. 6
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アミノ酸誘導体を用いた農業資材に関する研究
2024.1 - 2024.12
共同研究 共同研究
大井 貴史
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Authorship：Principal investigator Grant type：Collaborative (industry/university)
Grant amount：\1430000 （ Direct Cost: \1100000 、 Indirect Cost：\330000 ）
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直截的分子変換を担う多機能光ラジカル触媒の創製
2021.4 - 2023.3
内藤記念科学奨励金・研究助成
大井 貴史
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Authorship：Principal investigator Grant type：Other
Grant amount：\3000000 （ Direct Cost: \3000000 ）
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ルイスラジカルイオン対の触媒化学
Grant number：19H00894 2019.4 - 2022.3
科学研究費補助金 基盤研究(A)
大井 貴史
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Authorship：Principal investigator Grant type：Competitive
Grant amount：\45500000 （ Direct Cost: \35000000 、 Indirect Cost：\10500000 ）
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ハイブリッド触媒系による立体分岐型不斉合成
Grant number：17H06446 2017.6 - 2022.3
科学研究費補助金 新学術領域研究(研究領域提案型)
大井貴史
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Authorship：Principal investigator Grant type：Competitive
Grant amount：\144950000 （ Direct Cost: \111500000 、 Indirect Cost：\33450000 ）
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Development of Molecular Technology for Ideal Chemical Transformations
2013.10 - 2019.3
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Grant type：Competitive
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サスティナブル化学合成を担うイオン性非金属触媒の設計と機能創出
2011.2 - 2014.3
先端研究助成基金助成金（最先端・次世代研究開発支援プログラム）
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Grant type：Competitive
KAKENHI (Grants-in-Aid for Scientific Research)
KAKENHI (Grants-in-Aid for Scientific Research) 12
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Grant number：23K17914 2023.6 - 2025.3
科学研究費助成事業 挑戦的研究(萌芽)
大井 貴史
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Authorship：Principal investigator
Grant amount：\6500000 （ Direct Cost: \5000000 、 Indirect Cost：\1500000 ）
静電的な相互作用などの非共有結合性の相互作用を利用したイオン性化学種の反応性や立体化学の制御とは全く異なり、ラジカル種の発生および結合形成の各段階を制御するための信頼性と汎用性を備えた触媒的な方法論はほとんど確立されていない。本研究では、水素原子移動触媒と基質認識を担う分子触媒に電荷を附与しイオン対型ラジカル触媒を組み上げるという戦略に基づき、C(sp3)－H結合の切断を起点とした選択的な分子変換法を開拓する。
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Grant number：23H04907 2023.4 - 2028.3
科学研究費助成事業 学術変革領域研究(A)
大井 貴史
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Authorship：Principal investigator
Grant amount：\145990000 （ Direct Cost: \112300000 、 Indirect Cost：\33690000 ）
天然に豊富に存在する多彩な物質を炭素資源として活用するためには、有機分子に遍在するC-H結合の直接的な変換法の開拓、ならびにそれら変換反応の制御を担う触媒の創製が必須となる。本計画研究では、主として水素原子移動から進行するラジカル反応の開発に焦点を当て、C-H結合切断と続く結合形成を制御するための触媒・方法論を開拓することで、官能基を必要としない化学合成を確立する。具体的には、酸化剤を必要としないアクセプターレス脱水素型クロスカップリングや、飽和炭化水素の脱水素反応によって生成するオレフィンを標的とした選択的分子変換反応を実現する。
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Green Catalysis Science for Renovating Transformation of Carbon-Based Resources
Grant number：23H04901 2023.4 - 2028.3
Grants-in-Aid for Scientific Research Grant-in-Aid for Transformative Research Areas (A)
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Authorship：Principal investigator
Grant amount：\49660000 （ Direct Cost: \38200000 、 Indirect Cost：\11460000 ）
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Grant number：23H00296 2023.4 - 2026.3
科学研究費助成事業 基盤研究(A)
大井 貴史
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Authorship：Principal investigator
Grant amount：\47060000 （ Direct Cost: \36200000 、 Indirect Cost：\10860000 ）
結合の切断は、分子変換に欠かせない最も基本的な素過程である。炭素-ハロゲン(C-X）結合等の切断が容易な結合を利用する手法は分子変換を容易にするものの、適用できる基質が限定されるといったデメリットを生む。一方、有機分子に遍在するC-H結合の切断を起点とすれば、究極的にはあらゆる有機化合物を基質とする分子変換が可能になる。本研究では、2つの異なるC(sp3)-H結合の切断を伴うC-H/C-Hクロスカップリングを実現するための方法論を確立し、多様な化合物の自在変換に資する有機合成化学の開拓を目指す。
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Dynamic Element-Effect Design for Unconventional Molecular Functions
Grant number：22K21346 2022.12 - 2029.3
Grants-in-Aid for Scientific Research Fund for the Promotion of Joint International Research (International Leading Research )
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Authorship：Coinvestigator(s)
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Grant number：21K18957 2021.7 - 2023.3
日本学術振興会 科学研究費助成事業 挑戦的研究(萌芽)
大井 貴史
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Authorship：Principal investigator Grant type：Competitive
Grant amount：\6500000 （ Direct Cost: \5000000 、 Indirect Cost：\1500000 ）
ラジカルは化学反応における重要な反応性中間体であるが、クーロン力のような強い相互作用をもたず、その発生位置や反応性は基質の構造に大きく支配される。実際、イオン反応と比べて、ラジカル反応の制御に資する戦略や触媒は圧倒的に少なく、触媒的立体制御の成功例は未だ限定的である。特に、極性官能基をもたない単純な炭素ラジカルそのものの立体化学制御の実現には至っていない。本研究では、ラジカルイオンの可逆的な結合開裂に焦点を当て、アニオン捕捉型有機分子触媒による炭素ラジカルの全く新しい立体制御法を開拓する。
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ルイスラジカルイオン対の触媒化学
Grant number：19H00894 2019.4 - 2022.3
日本学術振興会 科学研究費補助金 基盤研究(A)
大井 貴史
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Authorship：Principal investigator Grant type：Competitive
Grant amount：\45500000 （ Direct Cost: \35000000 、 Indirect Cost：\10500000 ）
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ハイブリッド触媒系による立体分岐型不斉合成
Grant number：17H06446 2017.6 - 2022.3
文部科学省 科学研究費補助金 新学術領域研究
大井 貴史
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Authorship：Principal investigator Grant type：Competitive
Grant amount：\144950000 （ Direct Cost: \111500000 、 Indirect Cost：\33450000 ）
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真の自在化学変換を担う分子技術の創出
Grant number：JPMJCR13L2 2013.4 - 2018.3
科学研究費補助金 CREST
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サスティナブル化学合成を担うイオン性非金属触媒の設計と機能創出
Grant number：GR050 2011.2 - 2014.3
日本学術振興会 最先端・次世代研究開発支援プログラム 最先端・次世代研究開発支援プログラム
大井 貴史
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Authorship：Principal investigator
Grant amount：\167700000 （ Direct Cost: \129000000 、 Indirect Cost：\38700000 ）
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機能性イオン対協奏作用型有機分子触媒系の構築と応用
2008.4 - 2010.3
科学研究費補助金 特定領域研究「協奏機能触媒」
大井貴史
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Authorship：Principal investigator
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新規基質認識型キラル有機強塩基触媒の創製と応用
2007.4 - 2009.3
科学研究費補助金 特定領域研究（公募，A01），課題番号：19020022
大井 貴史
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Authorship：Principal investigator
Industrial property rights
Industrial property rights 11
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軸不斉を有する光学活性な４級アンモニウム塩を相間移動触媒として用いるβ-ヒドロキシアミノ酸誘導体の製造方法
丸岡 啓二，大井 貴史
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Applicant：長瀬産業株式会社
Date applied：2002
Announcement no：特開2003-327566
Patent/Registration no：特-4217085 Date registered：2009.1
Country of applicant：Domestic
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Chiral tetraaminophosphonium salts, catalyst for asymmetric synthesis and method for producing chiral beta-nitroalcohol
More details
Date applied：2009
Announcement no：US-A1-2009131716-2009-05-21
Country of applicant：Foreign country
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Preparation of optically active tetraaminophosphonium salts, catalysts for the asymmetric synthesis reactions, asymmetric synthesis reaction, and asymmetric-synthesis method of tetrasubstituted .alpha.- amino-acid containing peptide.
More details
Date applied：2008.9
Announcement no：JP-A-2010059133
Country of applicant：Domestic
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Catalyst capable of allowing Strecker reaction to proceed stereoselectively and method for stereoselectively producing .alpha.-aminonitrile derivative using the same.
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Date applied：2006
Announcement no：WO-A1-2007074553
Country of applicant：Foreign country
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光学活性なビシナルジアミンおよびその製造方法
丸岡 啓二，大井 貴史
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Applicant：長瀬産業株式会社
Date applied：2004
Announcement no：特開2005-232103
Date registered：2005
Country of applicant：Domestic
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光学活性な3-ニトロアルキルマロン酸エステル誘導体の製造方法
丸岡 啓二，大井 貴史
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Applicant：長瀬産業株式会社
Date applied：2004
Announcement no：特開2005-263664
Date registered：2005
Country of applicant：Domestic
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光学活性な3-アミノアスパラギン酸誘導体の製造方法
丸岡 啓二，大井 貴史
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Applicant：長瀬産業株式会社
Date applied：2004
Announcement no：特開2005-255610
Date registered：2005
Country of applicant：Domestic
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Quaternary ammonium bifluoride compound and process for producing chiral nitroalcohol.
More details
Date applied：2003
Announcement no：WO-A1-2004076459
Country of applicant：Foreign country
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光学活性3,5-ジヒドロ-4H-ジナフト[2,1-c:1’,2’-e]アゼピンおよびそのシュウ酸塩の製造方法
丸岡 啓二，大井 貴史，生中 雅也，奥田 佳朗
More details
Applicant：長瀬産業株式会社，ナガセケムテックス株式会社
Date applied：2003
Announcement no：特開2005-15402
Date registered：2005
Country of applicant：Domestic
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γ-ニトロカルボニル化合物の製造方法
丸岡 啓二，大井 貴史
More details
Applicant：長瀬産業株式会社
Date applied：2003
Announcement no：特開2004-352708
Date registered：2004
Country of applicant：Domestic
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Process for producing optically active .alpha.-substituted cysteine or salt thereof, intermediate therefor, and process for producing the same.
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Announcement no：WO-A1-2004031163
Date registered：2003
Country of applicant：Foreign country
Teaching Experience (On-campus)
Teaching Experience (On-campus) 195
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卒業研究A
2020
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卒業研究B
2020
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化学生命工学序論
2020
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化学生命工学演習
2020
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Organic Chemistry 4 with Exercises
2020
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有機・高分子化学基礎論
2020
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Seminar on Molecular Chemistry 1A
2020
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Seminar on Molecular Chemistry 1B
2020
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Seminar on Molecular Chemistry 1C
2020
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Seminar on Molecular Chemistry 1D
2020
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Advanced Experiments and Exercises in Molecular Chemistry I
2020
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Advanced Experiments and Exercises in Molecular Chemistry II
2020
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Seminar on Molecular Chemistry 2A
2020
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Seminar on Molecular Chemistry 2B
2020
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Seminar on Molecular Chemistry 2C
2020
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Seminar on Molecular Chemistry 2D
2020
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Seminar on Molecular Chemistry 2E
2020
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応用有機化学特別実験及び演習II
2019
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有機化学4及び演習
2019
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応用有機化学セミナー2E
2019
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応用有機化学基礎論
2019
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応用有機化学セミナー2D
2019
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応用有機化学特別実験及び演習I
2019
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応用有機化学セミナー2C
2019
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応用有機化学セミナー2B
2019
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応用有機化学セミナー2A
2019
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応用有機化学セミナー1D
2019
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応用有機化学セミナー1C
2019
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応用有機化学セミナー1B
2019
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応用有機化学セミナー1A
2019
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有機化学4及び演習
2018
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応用有機化学基礎論
2018
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応用有機化学特別実験及び演習I
2018
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応用有機化学特別実験及び演習II
2018
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応用有機化学セミナー2E
2018
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応用有機化学セミナー2D
2018
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応用有機化学セミナー2C
2018
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応用有機化学セミナー2B
2018
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応用有機化学セミナー2A
2018
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応用有機化学セミナー1D
2018
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応用有機化学セミナー1C
2018
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応用有機化学セミナー1B
2018
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応用有機化学セミナー1A
2018
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有機化学4及び演習
2017
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応用有機化学基礎論
2017
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応用有機化学特別実験及び演習I
2017
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応用有機化学特別実験及び演習II
2017
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応用有機化学セミナー2E
2017
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応用有機化学セミナー2D
2017
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応用有機化学セミナー2C
2017
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応用有機化学セミナー2B
2017
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応用有機化学セミナー2A
2017
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応用有機化学セミナー1D
2017
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応用有機化学セミナー1C
2017
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応用有機化学セミナー1B
2017
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応用有機化学セミナー1A
2017
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有機化学序論
2016
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有機化学Ⅳ
2016
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応用有機化学特別実験及び演習
2016
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応用有機化学セミナー2E
2016
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応用有機化学セミナー2D
2016
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応用有機化学セミナー2C
2016
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応用有機化学セミナー2B
2016
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応用有機化学セミナー2A
2016
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応用有機化学セミナー1D
2016
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応用有機化学セミナー1C
2016
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応用有機化学セミナー1B
2016
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応用有機化学セミナー1A
2016
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有機化学序論
2015
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有機化学Ⅳ
2015
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応用有機化学特別実験及び演習
2015
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応用有機化学セミナー2E
2015
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応用有機化学セミナー2D
2015
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応用有機化学セミナー2C
2015
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応用有機化学セミナー2B
2015
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応用有機化学セミナー2A
2015
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応用有機化学セミナー1D
2015
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応用有機化学セミナー1C
2015
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応用有機化学セミナー1B
2015
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応用有機化学セミナー1A
2015
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有機化学序論
2014
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有機化学Ⅳ
2014
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応用有機化学特別実験及び演習
2014
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応用有機化学セミナー2E
2014
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応用有機化学セミナー2D
2014
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応用有機化学セミナー2C
2014
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応用有機化学セミナー2B
2014
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応用有機化学セミナー2A
2014
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応用有機化学セミナー1D
2014
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応用有機化学セミナー1C
2014
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応用有機化学セミナー1B
2014
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応用有機化学セミナー1A
2014
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有機合成化学
2013
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有機化学序論
2013
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有機化学Ⅳ
2013
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応用有機化学特別実験及び演習
2013
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応用有機化学セミナー2E
2013
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応用有機化学セミナー2D
2013
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応用有機化学セミナー2C
2013
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応用有機化学セミナー2B
2013
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応用有機化学セミナー2A
2013
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応用有機化学セミナー1D
2013
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応用有機化学セミナー1C
2013
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応用有機化学セミナー1B
2013
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応用有機化学セミナー1A
2013
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有機合成化学
2012
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有機化学序論
2012
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有機化学Ⅳ
2012
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応用有機化学特別実験及び演習
2012
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応用有機化学基礎論
2012
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応用有機化学セミナー2E
2012
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応用有機化学セミナー2D
2012
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応用有機化学セミナー2C
2012
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応用有機化学セミナー2B
2012
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応用有機化学セミナー2A
2012
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応用有機化学セミナー1D
2012
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応用有機化学セミナー1C
2012
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応用有機化学セミナー1B
2012
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応用有機化学セミナー1A
2012
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応用有機化学セミナー1A
2011
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応用有機化学セミナー1B
2011
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有機化学序論
2011
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有機化学Ⅳ
2011
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応用有機化学特別実験及び演習
2011
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応用有機化学基礎論
2011
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応用有機化学セミナー2D
2011
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応用有機化学セミナー2E
2011
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応用有機化学セミナー2C
2011
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応用有機化学セミナー2B
2011
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応用有機化学セミナー2A
2011
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応用有機化学セミナー1D
2011
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応用有機化学セミナー1C
2011
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有機化学Ⅳ
2010
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応用有機化学特別実験及び演習
2010
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応用有機化学セミナー2D
2010
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応用有機化学セミナー2B
2010
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応用有機化学セミナー1D
2010
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応用有機化学セミナー1B
2010
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応用有機化学セミナー2E
2010
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応用有機化学セミナー2C
2010
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応用有機化学セミナー2A
2010
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応用有機化学セミナー1C
2010
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応用有機化学セミナー1A
2010
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応用有機化学基礎論
2010
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有機合成化学
2010
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有機化学序論
2010
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有機化学序論
2009
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応用有機化学特別実験及び演習
2009
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応用有機化学セミナー2D
2009
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応用有機化学セミナー2B
2009
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応用有機化学セミナー1D
2009
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応用有機化学セミナー1B
2009
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応用有機化学セミナー2E
2009
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応用有機化学セミナー2C
2009
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応用有機化学セミナー2A
2009
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応用有機化学セミナー1C
2009
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応用有機化学セミナー1A
2009
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応用有機化学基礎論
2009
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有機化学４
2009
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基礎セミナー
2008
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有機化学序論
2008
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応用有機化学セミナー2E
2008
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応用有機化学セミナー2D
2008
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応用有機化学セミナー2C
2008
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応用有機化学セミナー2B
2008
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応用有機化学セミナー2A
2008
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応用有機化学特別実験及び演習
2008
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応用有機化学セミナー1D
2008
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応用有機化学セミナー1C
2008
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応用有機化学セミナー1B
2008
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応用有機化学セミナー1A
2008
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応用有機化学基礎論
2008
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有機化学iV
2008
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有機合成化学
2008
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基礎セミナーＡ
2007
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応用有機化学セミナー2D
2007
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応用有機化学セミナー2B
2007
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応用有機化学セミナー2E
2007
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応用有機化学セミナー2C
2007
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応用有機化学セミナー2A
2007
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有機化学序論
2007
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応用有機化学セミナー1D
2007
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応用有機化学セミナー1C
2007
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応用有機化学セミナー1B
2007
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応用有機化学セミナー1A
2007
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応用有機化学基礎論
2007
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有機化学iV
2007
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有機合成化学
2007
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基礎セミナー
2007
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有機反応化学
2007
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有機化学序論
2007
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有機化学Ⅳ
2007
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有機化学序論
2006
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卒業研究A
2021
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卒業研究B
2021
Academic Activities
Academic Activities 1
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Associate Editor for ACS Catalysis International contribution
Role(s)：Review, evaluation, Peer review
American Chemical Society 2015.4
More details
Type：Peer review