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タイトル: | Enhanced Molecular Recognition through Substrate–Additive Complex Formation in N-Heterocyclic-Carbene-Catalyzed Kinetic Resolution of α-Hydroxythioamides |
著者: | Wang, Yinli Yamauchi, Akiho Hashimoto, Keiji Fujiwara, Tatsuya Inokuma, Tsubasa Mitani, Yuta Ute, Koichi Kuwano, Satoru Yamaoka, Yousuke Takasu, Kiyosei https://orcid.org/0000-0002-1798-7919 (unconfirmed) Yamada, Ken-ichi |
著者名の別形: | 鍬野, 哲 山岡, 庸介 高須, 清誠 |
キーワード: | organocatalysis molecular recognition catalytic kinetic resolution α-hydroxythioamide N-heterocyclic carbene |
発行日: | 20-May-2022 |
出版者: | American Chemical Society (ACS) |
誌名: | ACS Catalysis |
巻: | 12 |
号: | 10 |
開始ページ: | 6100 |
終了ページ: | 6107 |
抄録: | We describe a new way of understanding enhanced molecular recognition through substrate–additive complex formation and the development of the first catalytic kinetic resolution of α-hydroxythioamides, which are versatile synthetic building blocks, using chiral N-heterocyclic carbene-catalyzed enantioselective acylation assisted by a carboxylate additive. Mass spectrometry provided evidence for the role of the additive, which forms a hydrogen-bonded complex with α-hydroxythioamide, resulting in both rate and selectivity enhancements. The synthetic applications of the resolved α-hydroxythioamides highlight the usefulness of the developed method. |
著作権等: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, Copyright © 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.2c01579. The full-text file will be made open to the public on May 6, 2023 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
URI: | http://hdl.handle.net/2433/274668 |
DOI(出版社版): | 10.1021/acscatal.2c01579 |
出現コレクション: | 学術雑誌掲載論文等 |
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