Updated on 2021/04/28

写真a

 
OOI Takashi
 
Organization
Institute of Transformative Bio-Molecules Professor
Graduate School of Engineering
Title
Professor
External link

Degree 1

  1. Ph.D. ( 1994.3   Nagoya University ) 

Research Areas 1

  1. Others / Others  / Synthetic Chemistry

Current Research Project and SDGs 1

  1. 有機イオン対の分子設計に基づく触媒機能の創出

Research History 8

  1. Institute of Transformative Bio-Molecules (ITbM) Professor

    2013.4

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    Country:Japan

  2. Professor (Nagoya University)

    2006.5

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  3. Associate Professor (Kyoto University)

    2001.1 - 2006.4

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    Country:Japan

  4. Lecturer (Hokkaido University)

    1998.6 - 2000.12

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    Country:Japan

  5. Assistant Professor (Hokkaido University)

    1995.6 - 1998.5

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    Country:Japan

  6. Postdoctoral Fellow (MIT)

    1994.6 - 1995.3

  7. 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

  8. 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

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Education 2

  1. Nagoya University   Graduate School, Division of Engineering   Department of Applied Chemistry

    1991.4 - 1994.3

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    Country: Japan

  2. Nagoya University   Graduate School, Division of Engineering   Department of Applied Chemistry

    1989.4 - 1991.3

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    Country: Japan

Professional Memberships 3

  1. Chemical Society of Japan

  2. The Society of Synthetic Organic Chemistry, Japan

  3. American Chemical Society

Awards 10

  1. 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

  2. 日本化学会進歩賞

    1999   日本化学会  

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    Country:Japan

  3. Theme Journal Award

    2006   Theme  

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    Country:Japan

  4. 日本学術振興会賞

    2011.3   日本学術振興会  

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    Country:Japan

  5. 第25回日本IBM科学賞

    2011.11   日本IBM  

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    Country:Japan

  6. Inoue Prize for Science

    2014.2  

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    Country:Japan

  7. Fellow of the Royal Society of Chemistry

    2014   Fellow of the Royal Society of Chemistry  

  8. 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

  9. 第一三共・創薬有機化学賞

    2017   第一三共  

  10. 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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Papers 180

  1. 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

  2. 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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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.0c09468

    Web of Science

    PubMed

  3. 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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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.202001637

    Web of Science

  4. 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

    Web of Science

  5. 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)  

    DOI: 10.1002/anie.201913555

    Web of Science

  6. 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)  

    DOI: 10.1021/acscatal.9b04491

    Web of Science

  7. Catalytic asymmetric synthesis of 5-membered alicyclic α-quaternary β-amino acids <i>via</i> [3 + 2]-photocycloaddition of α-substituted acrylates. Reviewed

    Kimura Y, Uraguchi D, Ooi T

    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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  8. Mannich-type allylic C-H functionalization of enol silyl ethers under photoredox-thiol hybrid catalysis Reviewed

    Nakashima Tsubasa, Ohmatsu Kohsuke, Ooi Takashi

    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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    PubMed

  9. 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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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/COM-20-S(K)32

  10. 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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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/d0cc04821f

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    PubMed

  11. 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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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ajoc.202000067

    Web of Science

  12. 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

    CiNii Article

  13. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.9b09556

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  14. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1007/s41061-019-0256-1

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  15. 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)  

    DOI: 10.1038/s41467-019-10641-y

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  16. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c9qo00197b

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  17. 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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  18. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/cl.190197

  19. 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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    <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>

    DOI: 10.18978/jscrp.54.1_49

    CiNii Article

  20. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1126/science.aau5445

  21. 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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  22. 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)  

    DOI: 10.1246/bcsj.20180098

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  23. 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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    DOI: 10.1021/jacs.7b12949

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  24. 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)  

    DOI: 10.1002/anie.201800057

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  25. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/cl.180031

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  26. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.7b13433

  27. 丸岡啓二先生に日本学士院賞

    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)  

    DOI: 10.5059/yukigoseikyokaishi.76.565

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  28. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/C7CC07122A

  29. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c7sc01524k

  30. 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

  31. 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

  32. 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

  33. 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)  

    DOI: 10.1021/acscatal.7b00265

  34. 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

  35. [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)  

    DOI: 10.1246/bcsj.20170040

  36. 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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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0036-1558958

  37. 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

  38. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.6b02572

  39. 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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  40. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3762/bjoc.12.199

  41. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/cl.160158

  42. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0035-1561403

  43. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/bcsj.20160053

  44. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.6b00445

  45. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.5b09329

  46. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/C4CC10261D

  47. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.201503928

  48. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/cl.150581

  49. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/C5SC02170G

  50. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/NCHEM.1796

  51. 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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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/cs501369z

  52. 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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    DOI: 10.1016/j.tet.2013.12.086

  53. 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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    DOI: 10.3987/COM-13-S(S)121

  54. 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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    DOI: 10.1039/C3CC49338E

  55. 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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    DOI: 10.1055/s-0033-1340818

  56. 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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    DOI: 10.1039/C3CC49477B

  57. 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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    DOI: 10.1039/C4SC01032A

  58. 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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    DOI: 10.1039/C4CC06081D

  59. 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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    DOI: 10.1002/asia.201402943

  60. Highly Stereoselective Michael Addition of Azlactones to Electron-Deficient Triple Bonds under P-Spiro Chiral Iminophosphorane Catalysis: Importance of Protonation Pathway Reviewed

    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

  61. 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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    DOI: 10.1021/ja406999p

  62. 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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    DOI: 10.1021/ja411647x

  63. 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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    DOI: 10.1021/ja403491j

  64. Exploiting the Modularity of Ion-Paired Chiral Ligands for Palladium-Catalyzed Enantioselective Allylation of Benzofuran-2(3H)-ones Reviewed

    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

  65. Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles Reviewed

    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

  66. Chiral Ionic Brønsted Acid-Achiral Brønsted Base Synergistic Catalysis for Asymmetric Sulfa-Michael Addition to Nitroolefins Reviewed

    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

  67. Nitroolefins as a Nucleophilic Component for Highly Stereoselective Aza-Henry Reaction under the Catalysis of Chiral Ammonium Betaines Reviewed

    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.

    DOI: 10.1002/chem.201201259

  68. 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

  69. Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates Reviewed

    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

  70. Ionic Nucleophilic Catalysis of Chiral Ammonium Betaines for Highly Stereoselective Aldol Reaction from Oxindole-Derived Vinylic Carbonates Reviewed

    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

  71. 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.

    DOI: 10.1002/anie.201200559

  72. 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

  73. 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

  74. 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.

    DOI: 10.1055/s-0030-1260541

  75. 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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  76. 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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  77. 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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    DOI: 10.1002/anie.201007752

  78. 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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  79. 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.

  80. 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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  81. 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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  82. 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.

  83. 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.

  84. 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.

  85. 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.

  86. 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.

  87. 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.

  88. 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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  89. 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.

  90. *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.

  91. 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.

  92. 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.

  93. 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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  94. 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.

  95. *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.

  96. 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.

  97. *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.

  98. 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.

  99. 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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  100. *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.

  101. 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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  102. 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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  103. *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.

  104. 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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  105. 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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  106. 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.

  107. 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.

  108. 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.

  109. 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.

  110. 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.

  111. 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.

  112. 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.

  113. 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.

  114. 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.

  115. 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.

  116. 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.

  117. 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.

  118. 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.

  119. 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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  120. 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.

  121. 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.

  122. 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.

  123. 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.

  124. 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.

  125. 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.

  126. 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.

  127. 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.

  128. 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.

  129. 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.

  130. 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.

  131. 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.

  132. 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.

  133. 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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  134. 「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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  135. 「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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  136. 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.

  137. 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.

  138. 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.

  139. 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.

  140. 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.

  141. 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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  142. 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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  143. 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-disubstitute&shy;d 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 benzophenon&shy;e Schiff base.

  144. 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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  145. 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).

  146. 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.

  147. 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.

  148. 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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  149. 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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  150. 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.

  151. 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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  152. 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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  153. "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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  154. 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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  155. 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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  156. 「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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  157. 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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  158. 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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  159. 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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  160. 「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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  161. 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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  162. 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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  163. 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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  164. 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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  165. 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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  166. 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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  167. Exceptionally Bulky Lewis Acidic Reagent, MAD. Reviewed

    Ooi, Takashi; Maruoka, Keiji

    Rev. Heteroatom Chem.   Vol. 18   page: 61-85   1998

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  168. 「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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  169. 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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  170. 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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  171. 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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  172. 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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  173. 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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  174. (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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  175. 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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  176. 「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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  177. 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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  178. 「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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  179. 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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  180. 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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▼display all

Books 25

  1. Organic Molecular Catalysts in Radical Chemistry: Challenges Toward Selective Transformations

    Daisuke Uraguchi, Kohsuke Ohmatsu, Takashi Ooi( Role: Joint author)

    2019 

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    Language:English Book type:Scholarly book

  2. 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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    有機分子触媒の開発と工業利用

  3. Site-Selective Conjugate Addition through Catalytic Generation of Ion-Pairing Intermediates

    ( Role: Joint author)

    2016 

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    Language:English Book type:Scholarly book

  4. 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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    Language:English Book type:Scholarly book

  5. Asymmetric phase-transfer catalysis

    ( Role: Joint author)

    2013 

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    Language:English Book type:Scholarly book

  6. 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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    Language:English Book type:Scholarly book

    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

  7. Axially Chiral C2-Symmetric Catalysts

    ( Role: Joint author)

    2013 

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    Language:English Book type:Scholarly book

  8. Hydrogen-Bonding Catalysts Other than Ureas and Thioureas

    ( Role: Joint author)

    2012 

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    Language:English Book type:Scholarly book

  9. 6.1 C-C Bond Formation: Alkylation

    ( Role: Joint author)

    2012 

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    Language:English Book type:Scholarly book

  10. 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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    Language:English

  11. “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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    Language:English

  12. “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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    Language:English

  13. “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

  14. “Asymmetric Synthesis - The Essentials ” M. Christmann, S. Br&auml;se 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

  15. "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

  16. "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

  17. 「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

  18. 「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

  19. 「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

  20. 「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

  21. “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

  22. “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

  23. “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

  24. “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

  25. 「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

▼display all

Presentations 40

  1. 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  

  2. 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  

  3. 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  

  4. 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)  

  5. 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  

  6. 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  

  7. 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  

  8. 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  

  9. 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  

  10. 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  

  11. 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  

  12. 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  

  13. 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  

  14. 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)  

  15. 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)  

  16. 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  

  17. 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  

  18. 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  

  19. 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  

  20. 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  

  21. 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  

  22. 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  

  23. 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)  

  24. 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)  

  25. 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  

  26. 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)  

  27. 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  

  28. 「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  

  29. 「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  

  30. "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)  

  31. 「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  

  32. 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  

  33. 「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  

  34. 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)  

  35. 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  

  36. 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  

  37. 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  

  38. 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  

  39. 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  

  40. 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  

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Research Project for Joint Research, Competitive Funding, etc. 4

  1. 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 )

  2. 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 )

  3. Development of Molecular Technology for Ideal Chemical Transformations

    2013.10 - 2019.3

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    Grant type:Competitive

  4. 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) 4

  1. 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

  2. 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 )

  3. 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 

  4. 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 11

  1. 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  

  2. Chiral tetraaminophosphonium salts, catalyst for asymmetric synthesis and method for producing chiral beta-nitroalcohol

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    Date applied:2009

    Announcement no:US-A1-2009131716-2009-05-21 

    Country of applicant:Foreign country  

  3. 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.

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    Date applied:2008.9

    Announcement no:JP-A-2010059133 

    Country of applicant:Domestic  

  4. 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  

  5. 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  

  6. 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  

  7. 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  

  8. 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

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    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  

  9. 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  

  10. 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  

  11. Process for producing optically active .alpha.-substituted cysteine or salt thereof, intermediate therefor, and process for producing the same.

     More details

    Announcement no:WO-A1-2004031163 

    Date registered:2003 

    Country of applicant:Foreign country  

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Teaching Experience (On-campus) 193

  1. 卒業研究A

    2020

  2. 卒業研究B

    2020

  3. 化学生命工学序論

    2020

  4. 化学生命工学演習

    2020

  5. Organic Chemistry 4 with Exercises

    2020

  6. 有機・高分子化学基礎論

    2020

  7. Seminar on Molecular Chemistry 1A

    2020

  8. Seminar on Molecular Chemistry 1C

    2020

  9. Seminar on Molecular Chemistry 1B

    2020

  10. Seminar on Molecular Chemistry 1D

    2020

  11. Advanced Experiments and Exercises in Molecular Chemistry I

    2020

  12. Advanced Experiments and Exercises in Molecular Chemistry II

    2020

  13. Seminar on Molecular Chemistry 2A

    2020

  14. Seminar on Molecular Chemistry 2B

    2020

  15. Seminar on Molecular Chemistry 2C

    2020

  16. Seminar on Molecular Chemistry 2D

    2020

  17. Seminar on Molecular Chemistry 2E

    2020

  18. 応用有機化学特別実験及び演習II

    2019

  19. 有機化学4及び演習

    2019

  20. 応用有機化学セミナー2E

    2019

  21. 応用有機化学基礎論

    2019

  22. 応用有機化学セミナー2D

    2019

  23. 応用有機化学特別実験及び演習I

    2019

  24. 応用有機化学セミナー2C

    2019

  25. 応用有機化学セミナー2B

    2019

  26. 応用有機化学セミナー2A

    2019

  27. 応用有機化学セミナー1D

    2019

  28. 応用有機化学セミナー1C

    2019

  29. 応用有機化学セミナー1B

    2019

  30. 応用有機化学セミナー1A

    2019

  31. 有機化学4及び演習

    2018

  32. 応用有機化学基礎論

    2018

  33. 応用有機化学特別実験及び演習I

    2018

  34. 応用有機化学特別実験及び演習II

    2018

  35. 応用有機化学セミナー2E

    2018

  36. 応用有機化学セミナー2D

    2018

  37. 応用有機化学セミナー2C

    2018

  38. 応用有機化学セミナー2B

    2018

  39. 応用有機化学セミナー2A

    2018

  40. 応用有機化学セミナー1D

    2018

  41. 応用有機化学セミナー1C

    2018

  42. 応用有機化学セミナー1B

    2018

  43. 応用有機化学セミナー1A

    2018

  44. 有機化学4及び演習

    2017

  45. 応用有機化学基礎論

    2017

  46. 応用有機化学特別実験及び演習I

    2017

  47. 応用有機化学特別実験及び演習II

    2017

  48. 応用有機化学セミナー2E

    2017

  49. 応用有機化学セミナー2D

    2017

  50. 応用有機化学セミナー2C

    2017

  51. 応用有機化学セミナー2B

    2017

  52. 応用有機化学セミナー2A

    2017

  53. 応用有機化学セミナー1D

    2017

  54. 応用有機化学セミナー1C

    2017

  55. 応用有機化学セミナー1B

    2017

  56. 応用有機化学セミナー1A

    2017

  57. 有機化学序論

    2016

  58. 有機化学Ⅳ

    2016

  59. 応用有機化学特別実験及び演習

    2016

  60. 応用有機化学セミナー2E

    2016

  61. 応用有機化学セミナー2D

    2016

  62. 応用有機化学セミナー2C

    2016

  63. 応用有機化学セミナー2B

    2016

  64. 応用有機化学セミナー2A

    2016

  65. 応用有機化学セミナー1D

    2016

  66. 応用有機化学セミナー1C

    2016

  67. 応用有機化学セミナー1B

    2016

  68. 応用有機化学セミナー1A

    2016

  69. 有機化学序論

    2015

  70. 有機化学Ⅳ

    2015

  71. 応用有機化学特別実験及び演習

    2015

  72. 応用有機化学セミナー2E

    2015

  73. 応用有機化学セミナー2D

    2015

  74. 応用有機化学セミナー2C

    2015

  75. 応用有機化学セミナー2B

    2015

  76. 応用有機化学セミナー2A

    2015

  77. 応用有機化学セミナー1D

    2015

  78. 応用有機化学セミナー1C

    2015

  79. 応用有機化学セミナー1B

    2015

  80. 応用有機化学セミナー1A

    2015

  81. 有機化学序論

    2014

  82. 有機化学Ⅳ

    2014

  83. 応用有機化学特別実験及び演習

    2014

  84. 応用有機化学セミナー2E

    2014

  85. 応用有機化学セミナー2D

    2014

  86. 応用有機化学セミナー2C

    2014

  87. 応用有機化学セミナー2B

    2014

  88. 応用有機化学セミナー2A

    2014

  89. 応用有機化学セミナー1D

    2014

  90. 応用有機化学セミナー1C

    2014

  91. 応用有機化学セミナー1B

    2014

  92. 応用有機化学セミナー1A

    2014

  93. 有機合成化学

    2013

  94. 有機化学序論

    2013

  95. 有機化学Ⅳ

    2013

  96. 応用有機化学特別実験及び演習

    2013

  97. 応用有機化学セミナー2E

    2013

  98. 応用有機化学セミナー2D

    2013

  99. 応用有機化学セミナー2C

    2013

  100. 応用有機化学セミナー2B

    2013

  101. 応用有機化学セミナー2A

    2013

  102. 応用有機化学セミナー1D

    2013

  103. 応用有機化学セミナー1C

    2013

  104. 応用有機化学セミナー1B

    2013

  105. 応用有機化学セミナー1A

    2013

  106. 有機合成化学

    2012

  107. 有機化学序論

    2012

  108. 有機化学Ⅳ

    2012

  109. 応用有機化学特別実験及び演習

    2012

  110. 応用有機化学基礎論

    2012

  111. 応用有機化学セミナー2E

    2012

  112. 応用有機化学セミナー2D

    2012

  113. 応用有機化学セミナー2C

    2012

  114. 応用有機化学セミナー2B

    2012

  115. 応用有機化学セミナー2A

    2012

  116. 応用有機化学セミナー1D

    2012

  117. 応用有機化学セミナー1C

    2012

  118. 応用有機化学セミナー1B

    2012

  119. 応用有機化学セミナー1A

    2012

  120. 応用有機化学セミナー1A

    2011

  121. 応用有機化学セミナー1B

    2011

  122. 有機化学序論

    2011

  123. 有機化学Ⅳ

    2011

  124. 応用有機化学特別実験及び演習

    2011

  125. 応用有機化学基礎論

    2011

  126. 応用有機化学セミナー2D

    2011

  127. 応用有機化学セミナー2E

    2011

  128. 応用有機化学セミナー2C

    2011

  129. 応用有機化学セミナー2B

    2011

  130. 応用有機化学セミナー2A

    2011

  131. 応用有機化学セミナー1D

    2011

  132. 応用有機化学セミナー1C

    2011

  133. 有機化学Ⅳ

    2010

  134. 応用有機化学特別実験及び演習

    2010

  135. 応用有機化学セミナー2D

    2010

  136. 応用有機化学セミナー2B

    2010

  137. 応用有機化学セミナー1D

    2010

  138. 応用有機化学セミナー1B

    2010

  139. 応用有機化学セミナー2E

    2010

  140. 応用有機化学セミナー2C

    2010

  141. 応用有機化学セミナー2A

    2010

  142. 応用有機化学セミナー1C

    2010

  143. 応用有機化学セミナー1A

    2010

  144. 応用有機化学基礎論

    2010

  145. 有機合成化学

    2010

  146. 有機化学序論

    2010

  147. 有機化学序論

    2009

  148. 応用有機化学特別実験及び演習

    2009

  149. 応用有機化学セミナー2D

    2009

  150. 応用有機化学セミナー2B

    2009

  151. 応用有機化学セミナー1D

    2009

  152. 応用有機化学セミナー1B

    2009

  153. 応用有機化学セミナー2E

    2009

  154. 応用有機化学セミナー2C

    2009

  155. 応用有機化学セミナー2A

    2009

  156. 応用有機化学セミナー1C

    2009

  157. 応用有機化学セミナー1A

    2009

  158. 応用有機化学基礎論

    2009

  159. 有機化学4

    2009

  160. 基礎セミナー

    2008

  161. 有機化学序論

    2008

  162. 応用有機化学セミナー2E

    2008

  163. 応用有機化学セミナー2D

    2008

  164. 応用有機化学セミナー2C

    2008

  165. 応用有機化学セミナー2B

    2008

  166. 応用有機化学セミナー2A

    2008

  167. 応用有機化学特別実験及び演習

    2008

  168. 応用有機化学セミナー1D

    2008

  169. 応用有機化学セミナー1C

    2008

  170. 応用有機化学セミナー1B

    2008

  171. 応用有機化学セミナー1A

    2008

  172. 応用有機化学基礎論

    2008

  173. 有機化学iV

    2008

  174. 有機合成化学

    2008

  175. 基礎セミナーA

    2007

  176. 応用有機化学セミナー2D

    2007

  177. 応用有機化学セミナー2B

    2007

  178. 応用有機化学セミナー2E

    2007

  179. 応用有機化学セミナー2C

    2007

  180. 応用有機化学セミナー2A

    2007

  181. 有機化学序論

    2007

  182. 応用有機化学セミナー1D

    2007

  183. 応用有機化学セミナー1C

    2007

  184. 応用有機化学セミナー1B

    2007

  185. 応用有機化学セミナー1A

    2007

  186. 応用有機化学基礎論

    2007

  187. 有機化学iV

    2007

  188. 有機合成化学

    2007

  189. 基礎セミナー

    2007

  190. 有機反応化学

    2007

  191. 有機化学序論

    2007

  192. 有機化学Ⅳ

    2007

  193. 有機化学序論

    2006

▼display all