研究者詳細 - 安井　猛

論文 - 安井　猛

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Enantioselective Desymmetrization of Trifluoromethylated Tertiary Benzhydrols via Hydrogen-Acceptor-Free Ir-Catalyzed Dehydrogenative C-H Silylation: Decisive Role of the Trifluoromethyl Group. 査読有り

Yamamoto Y, Tadano R, Yasui T

JACS Au 4 巻 ( 2 ) 頁： 807 - 815 2024年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：JACS Au

Although the trifluoromethyl (CF3) group is one of the most important fluorinated groups owing to its significant ability to modulate pharmacological properties, constructing trifluoromethylated stereogenic centers in an enantioselective manner has been a formidable challenge. Herein, we report the development of the enantioselective desymmetrization of trifluoromethylated benzhydrols via intramolecular dehydrogenative silylation using Ir catalysts with chiral pyridine-oxazoline (PyOX) ligands. The produced benzoxasilol was transformed into several unsymmetrical benzhydrols via iododesilylation and subsequent transition-metal-catalyzed cross-coupling reactions. Moreover, the same Ir catalyst system was used for the kinetic resolution of unsymmetrical trifluoromethylated benzhydrols.

DOI： 10.1021/jacsau.3c00794

Scopus

PubMed

Cobalt/Organophotoredox Dual Catalysis-Enabled Cyclization of 1,5,10-Enediynes Involving Metallole-Mediated Remote C(sp3)-H Bond Activation Leading to Axially Chiral Alkenes 査読有り

Keiji Yamada, Nobuaki Koga, Takeshi Yasui, Yoshihiko Yamamoto

ACS Catalysis 2024年1月

[Development of Catalytic Cycloisomerization Reactions Enabling Construction of Polycyclic Frameworks Found in Bioactive Molecules]. 招待有り査読有り

Yasui T

Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 143 巻 ( 11 ) 頁： 889 - 895 2023年11月

担当区分：筆頭著者,　責任著者記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Yakugaku Zasshi

The transition-metal-catalyzed cycloisomerization of unsaturated compounds, such as alkynes, alkenes, allenes, and nitriles, is a powerful tool for constructing polycyclic frameworks found in many biologically active natural products and pharmaceuticals. However, this approach predominantly relies on precious transition metals, such as rhodium and iridium. Thus, the development of cycloisomerization reactions using less expensive, less toxic, and environmentally friendly transition metals that are abundantly found in the earth has attracted considerable attention in recent years. In this article, we reviewed our recent studies on the synthesis of various polycyclic compounds via cycloisomerization enabled by the cobalt/photoredox dual catalysis. Our research has demonstrated the excellent efficiency of the cobalt/photoredox dual catalyst system for the cycloisomerization of 1,6-diyne derivatives. We constructed tricyclic cyclohexadiene frameworks, which are found in many biologically active natural products such as 11-O-debenzoyltashironin, perforanoid A, and jiadifenolide, using 1,6,11-enediynes as substrates for the cobalt-catalyzed cycloisomerization. Using a chiral ligand, (S)-Segphos, we achieved an enantioselective reaction that allowed access to enantio-enriched tricyclic cyclohexadiene products. Furthermore, we discovered that a novel cascade cyclization of 1,6-diynyl esters, enabled by the cobalt/photoredox dual catalysis, provided various cyclic compounds via the formation of vinylallene intermediates.

DOI： 10.1248/yakushi.23-00127

Scopus

PubMed

Rh(III)-Catalyzed Highly Site- and Regio-Selective Alkenyl C–H Activation/Annulation of 4-Amino-2-Quinolones with Alkynes via Reversible Alkyne Insertion 査読有り

Naohiro Hirako, Takeshi Yasui, Yoshihiko Yamamoto

Chemical Science 2023年9月

Cycloaddition of Cyclopropenes with Alkynes via Carbon-Carbon Double Bond Cleavage Enabled by a Ruthenium Catalyst: Synthesis of Cyclopentadienes and Cycloheptatrienes 査読有り

Kikuchi Tomohiro, Yasui Takeshi, Yamamoto Yoshihiko

ACS CATALYSIS 13 巻 ( 14 ) 頁： 9656 - 9666 2023年7月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ACS Catalysis

Transition-metal-mediated carbon-carbon single-bond cleavage of cyclopropenes has been widely exploited in organic synthesis. However, the ring-opening of cyclopropenes via the cleavage of their carbon-carbon double bond remains a formidable challenge. Herein, we report an intramolecular cycloaddition of cyclopropenes with alkynes via cleavage of the carbon-carbon double bond of cyclopropenes enabled by a ruthenium catalyst to afford 1,2-fused cyclopentadienes, which are difficult to access by conventional synthetic methods. Density functional theory calculations indicate that the reaction proceeds via a cyclopropane-fused ruthenacycle that undergoes ring expansion to generate a six-membered cyclic biscarbenoid. We also synthesized fused cycloheptatrienes via the cycloaddition of cyclopropene-diynes.

DOI： 10.1021/acscatal.3c02543

Web of Science

Scopus

Trifluoromethylated Oxidopyridinium Betaines: Unique (5+2) Cycloaddition Selectivity Imposed by 2-or 6-Trifluoromethyl Groups 査読有り

Yamamoto Yoshihiko, Tazawa Syunji, Tadano Ryu, Yasui Takeshi

CHEMISTRY-AN ASIAN JOURNAL 18 巻 ( 10 ) 頁： e202300211 2023年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemistry - An Asian Journal

Despite the significant advances in trifluoromethylation methods, the synthesis of complex trifluoromethylated molecules, bearing a natural-product-like three-dimensional framework, remains as a formidable challenge. Therefore, the cycloaddition of unprecedented CF3-substituted oxidopyridinium betaines was investigated. After the methylation of trifluoromethylated pyridin-3-ols with methyl triflate, pyridinium ions generated in-situ were treated with triethylamine in the presence of N-methylmaleimide to produce trifluoromethylated 8-azabicyclo[3.2.1]octane derivatives via (5+2) cycloaddition of the corresponding oxidopyridinium betaines. Exo/endo-selectivity varied depending on the positions of the CF3 substituents; endo-products were preferred in the reactions of oxidopyridinium betaines with the CF3 group at the 2- or 6-positions, whereas the 5-CF3-substituted betaine exclusively produced an exo-product. Moreover, unique regio- and stereoselectivities have been observed in the reactions of 2- or 6-CF3-substituted oxidopyridinium betaines with vinyl sulfones and trans-1,2-disubstituted alkenes. To gain insight into the reactivity of trifluoromethylated oxidopyridinium betaines, computational investigations were also conducted.

DOI： 10.1002/asia.202300211

Web of Science

Scopus

PubMed

Oxidopyridinium Cycloadditions Revisited: A Combined Computational and Experimental Study on the Reactivity of 1-(2-Pyrimidyl)-3-oxidopyridinium Betaine 査読有り

Yoshihiko Yamamoto, Yudai Shizume, Syunji Tazawa, Takeshi Yasui

The Journal of Organic Chemistry 2023年3月

Construction of Diverse Poly cyclic Structures via Group 9 Metal-Catalyzed Cycloisomerization of 1,6-Diyne Derivatives 査読有り

Yasui T., Yamamoto Y.

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 81 巻 ( 2 ) 頁： 127 - 138 2023年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Polycyclic structures are found in many natural products and pharmaceuticals. The transition-metal-catalyzed cycloisomerization of unsaturated compounds is one of the most powerful methods for construction of polycyclic frameworks in a single operation. In particular, 1,6-diyne is the structural motif widely used for the cycloisomerization as it readily reacts with low-valent metal catalysts to form metallacyclopentadiene intermediates. However, this method has been mainly exploited for the synthesis of aromatic compounds such as benzenes and pyridines. This article describes our recent studies regarding the synthesis of various polycyclic structures including non-aromatic carbocycles, such as 5-6-5 tricyclic cyclohexadienes bearing a quaternary bridgehead carbon and tetralone-containing exocyclic dienes, via the group 9 metal-catalyzed cycloisomerization reaction of 1,6-diyne derivatives. In the course of our study, we elucidated that the cobalt/photoredox dual catalysis is very efficient for the cycloisomerization of 1,6-diyne derivatives such as enediynes. We also found a novel cascade cyclization of 1,6-diynyl esters to form various cyclic compounds through the formation of vinylallene intermediates.

DOI： 10.5059/yukigoseikyokaishi.81.127

Scopus

Concise Synthesis of Functionalized Cyclopentadienyl Rhodium(III) Complexes via Suzuki–Miyaura Cross Coupling 査読有り

Takeshi Yasui, Shouta Tanabe, Takuya Masueda, Yoshihiko Yamamoto

Synthesis 2022年11月

Combined Computational and Experimental Study on [5 + 2] Cycloaddition of 2-Trifluoromethylated Oxidopyrylium Species Leading to 1-(Trifluoromethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-ones 査読有り

Yoshihiko Yamamoto, Yuya Nakazato, Ryu Tadano, Takeshi Yasui

Journal of Organic Chemistry 2022年7月

Co-Catalyzed atom transfer radical addition of bromodifluoroacetamides, expanding the scope of radical difluoroalkylation 査読有り

Yoshihiko Yamamoto, Harufumi Suzuki, Eisuke Kuroyanagi, Keiji Yamada, Takeshi Yasui

Organic & Biomolecular Chemistry 2022年3月

Development of novel potent ligands for GPR85, an orphan G protein-coupled receptor expressed in the brain 査読有り

Aya Sakaki, Takeshi Yasui, Masashi Watanabe, Rine Tatsumi, Yoshihiko Yamamoto, Wataru Takano, Yuki Tani, Izumi Okamura, Hirokazu Hirai, Shigeki Takeda

Genes to Cells 2022年2月

Cobalt/Organophotoredox Dual-Catalysis-Enabled Cascade Cyclization of 1,6-Diynyl Esters via Formal 1,8-Acyloxy Migration 査読有り

Takeshi Yasui, Keiji Yamada, Rine Tatsumi, Yoshihiko Yamamoto

ACS Catalysis 2021年9月

Catalyst-Free Csp−Csp3 Cross-Coupling of Bromodifluoroacetamides with 1-Iodoalkynes under Visible-Light Irradiation 査読有り

Yoshihiko Yamamoto, Eisuke Kuroyanagi, Harufumi Suzuki, Takeshi Yasui

Advanced Synthesis & Catalysis 2021年9月

Highly Enantioselective [2+2+2] Cycloaddition of Enediynes Enabled by Cobalt/Organophotoredox Cooperative Catalysis 査読有り

Takeshi Yasui, Rine Tatsumi, and Yoshihiko Yamamoto

ACS Catalysis 2021年7月

Enantioselective Construction of 5-6-5 Tricyclic Lactone Framework Bearing a Quaternary Bridgehead Carbon via Rh-Catalyzed Asymmetric [2+2+2] Cycloaddition of Enediynes 査読有り

Takeshi Yasui, Yuya Nakazato, Koutarou Kurisaki, and Yoshihiko Yamamoto

Advanced Synthesis & Catalysis 2021年7月

Synthesis of Benzo-Fused Cyclic Ketones via Metal-Free Ring Expansion of Cyclopropanols Enabled by Proton-Coupled Electron Transfer 査読有り

Tomohiro Kikuchi, Keiji Yamada, Takeshi Yasui, Yoshihiko Yamamoto

Organic Letters 2021年6月

Synthesis of difluoromethylated diarylmethanes via Fe(OTf)3-catalyzed Friedel–Crafts reaction of 2,2-difluoro-1-arylethyl phosphates 査読有り

Yoshihiko Yamamoto, Tomoya Takase, Eisuke Kuroyanagi, Takeshi Yasui

Chemical Communications 2021年3月

A Combined Experimental and Computational Study on the Palladium-Catalyzed Sequential [2+2+1] Spirocyclization/Arene C–H Activation of 4-Iodo-2-quinolones with Diphenylacetylene 査読有り

Yoshihiko Yamamoto, Naohiro Hirako, Takeshi Yasui

Bulletin of the Chemical Society of Japan 2021年2月

Synthesis of 1-(Difluoromethyl)alk-1-enes via Palladium-Catalyzed S(N)2 '-Type Substitution Reaction of Difluoromethylated Allylic Phosphates with 1,3-Dicarbonyl Compounds and Imides 査読有り

86 巻 ( 1 ) 頁： 1053 - 1064 2021年1月

Rhodium-catalyzed cycloisomerization of ester-tethered 1,6-diynes with cyclopropanol moiety leading to tetralone/exocyclic diene hybrid molecules. 査読有り

Yasui T, Kikuchi T, Yamamoto Y

Chemical communications (Cambridge, England) 2020年9月

Palladium-Catalyzed [3+2] and [2+2+2] Annulations of 4-Iodo-2-quinolones with Activated Alkynes through Selective C-H Activation 査読有り

Yamamoto Yoshihiko, Jiang Jiyue, Yasui Takeshi

CHEMISTRY-A EUROPEAN JOURNAL 26 巻 ( 17 ) 頁： 3749-3757 2020年2月

Novel Pure αVβ3 Integrin Antagonists That Do Not Induce Receptor Extension, Prime the Receptor, or Enhance Angiogenesis at Low Concentrations. 査読有り

Li J, Fukase Y, Shang Y, Zou W, Muñoz-Félix JM, Buitrago L, van Agthoven J, Zhang Y, Hara R, Tanaka Y, Okamoto R, Yasui T, Nakahata T, Imaeda T, Aso K, Zhou Y, Locuson C, Nesic D, Duggan M, Takagi J, Vaughan RD, Walz T, Hodivala-Dilke K, Teitelbaum SL, Arnaout MA, Filizola M, Foley MA, Coller BS

2 巻 ( 6 ) 頁： 387-401 2019年12月

Synthesis of (Difluoromethyl)cycloalkenes from 2-Cycloalkenones by Utilizing Phospha-Brook Rearrangement 査読有り

Yamamoto Yoshihiko, Ishida Yuki, Takamizu Yosuke, Yasui Takeshi

ADVANCED SYNTHESIS & CATALYSIS 361 巻 ( 16 ) 頁： 3739-3743 2019年8月

SYNTHESIS OF gamma-DIFLUOROMETHYLATED TETRONATE DERIVATIVES FROM SQUARATES USING DIFLUOROMETHYLPHOSPHONATE

Yamamoto Yoshihiko, Ishida Yuki, Kurohara Takashi, Shibuya Masatoshi, Yasui Takeshi

HETEROCYCLES 99 巻 ( 1 ) 頁： 363-378 2019年4月

The vinylogous Catellani reaction: a combined computational and experimental study

Yamamoto Y., Murayama T., Jiang J., Yasui T., Shibuya M.

CHEMICAL SCIENCE 9 巻 ( 5 ) 頁： 1191-1199 2018年2月

Combined Experimental and Computational Study on Catalytic Cyclocoupling of Epxides and CO2 Using Porphyrin-Based Cu(II) Metal-Organic Frameworks with 2D Coordination Networks 査読有り

Tsukasa Murayama, Masayuki Asano, Tetsushi Ohmura, Arimitsu Usuki, Takeshi Yasui, Yoshihiko Yamamoto

Bull. Chem. Soc. Jpn. 91 巻頁： 383-390 2018年

Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative Spirolactonization of Naphthol Derivatives

Uyanik Muhammet, Yasui Takeshi, Ishihara Kazuaki

JOURNAL OF ORGANIC CHEMISTRY 82 巻 ( 22 ) 頁： 11946-11953 2017年11月

Discovery of a novel B-cell lymphoma 6 (BCL6)-corepressor interaction inhibitor by utilizing structure-based drug design.

Yasui T, Yamamoto T, Sakai N, Asano K, Takai T, Yoshitomi Y, Davis M, Takagi T, Sakamoto K, Sogabe S, Kamada Y, Lane W, Snell G, Iwata M, Goto M, Inooka H, Sakamoto JI, Nakada Y, Imaeda Y

Bioorganic & medicinal chemistry 25 巻 ( 17 ) 頁： 4876-4886 2017年9月

Hydrogen Bonding and Alcohol Effects in Asymmetric Hypervalent Iodine Catalysis: Enantioselective Oxidative Dearomatization of Phenols 査読有り

Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara

Angewandte Chemie International Edition 52 巻 ( 35 ) 頁： 9215-9218 2013年

In Situ Generated (Hypo)Iodite Catalysts for the Direct alpha-Oxyacylation of Carbonyl Compounds with Carboxylic Acids 査読有り

Dr. Muhammet Uyanik, Daisuke Suzuki, Takeshi Yasui, Kazuaki Ishihara

Angewandte Chemie International Edition 50 巻 ( 23 ) 頁： 5331-5334 2011年

Enantioselective Kita Oxidative Spirolactonization Catalyzed by In Situ Generated Chiral Hypervalent Iodine(III) Species 査読有り

Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara

Angewandte Chemie International Edition 49 巻頁： 2175-2177 2010年

Chiral Hypervalent Iodine-Catalyzed Enantioselective Oxidative Kita Spirolactonization of 1-Naphthol Derivatives and One-Pot Diastereoselective Oxidation to Epoxyspirolactones 招待有り査読有り

Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara

Tetrahedron 66 巻 ( 31 ) 頁： 5841-5851 2010年

Quaternary Ammonium (Hypo)iodite Catalysis for Enantioselective Oxidative Cycloetherification 査読有り

Muhammet Uyanik, Hiroaki Okamoto, Takeshi Yasui, Kazuaki Ishihara

Science 328 巻 ( 5984 ) 頁： 1376-1379 2010年

Hypervalent Iodine-Catalyzed Oxylactonization of Ketocarboxylic Acids to Ketolactones 招待有り査読有り

Muhammet Uyanik, Takeshi Yasui, Kazuaki Ishihara

Bioorganic & Medicinal Chemistry Letters 19 巻頁： 3848-3851 2009年

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