ID | 65231 |
フルテキストURL | |
著者 |
Rozsar, Daniel
Department of Chemistry, University of Oxford, Chemistry Research Laboratory
Farley, Alistair J. M.
Department of Chemistry, University of Oxford, Chemistry Research Laboratory
McLauchlan, Iain
Department of Chemistry, University of Oxford, Chemistry Research Laboratory
Shennan, Benjamin D. A.
Department of Chemistry, University of Oxford, Chemistry Research Laboratory
Yamazaki, Ken
Division of Applied Chemistry, Okayama University
Dixon, Darren J.
Department of Chemistry, University of Oxford, Chemistry Research Laboratory
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抄録 | Herein we describe the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated α,β-unsaturated esters, catalyzed by a bifunctional iminophosphorane (BIMP) superbase. The transformation provides the most direct access to pharmaceutically relevant enantioenriched γ-nitroesters, utilizing feedstock chemicals, with unprecedented selectivity. The methodology exhibits a broad substrate scope, including β-(fluoro)alkyl, aryl and heteroaryl substituted electrophiles, and was successfully applied on a gram scale with reduced catalyst loading, and, additionally, catalyst recovery was carried out. The formal synthesis of a range of drug molecules, and an enantioselective synthesis of (S)-rolipram were achieved. Additionally, computational studies revealed key reaction intermediates and transition state structures, and provided rationale for high enantioselectivities, in good agreement with experimental results.
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キーワード | Asymmetric Catalysis
C-C Bond Formation
Conjugate Addition
Enantioselective Synthesis
Organocatalysis
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発行日 | 2023-04-13
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出版物タイトル |
Angewandte Chemie International Edition
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巻 | 62巻
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号 | 21号
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出版者 | Wiley
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開始ページ | e202303391
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ISSN | 1433-7851
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資料タイプ |
学術雑誌論文
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言語 |
英語
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OAI-PMH Set |
岡山大学
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著作権者 | © 2023 The Authors.
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論文のバージョン | publisher
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PubMed ID | |
DOI | |
Web of Science KeyUT | |
関連URL | isVersionOf https://doi.org/10.1002/anie.202303391
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ライセンス | http://creativecommons.org/licenses/by/4.0/
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