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通过协同光氧化还原/布朗斯特酸催化实现烯基呋喃的不对称酮烷基化/重排反应

Asymmetric Ketoalkylation/Rearrangement of Alkyenlfurans via Synergistic Photoredox/Brønsted Acid Catalysis.

作者信息

Wei Jie, Tang Yurong, Yang Qian, Li Hongxiang, He Dongxian, Cai Yunfei

机构信息

School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China.

Chongqing Medical and Pharmaceutical College, Chongqing 401331, China.

出版信息

Org Lett. 2022 Nov 4;24(43):7928-7933. doi: 10.1021/acs.orglett.2c03040. Epub 2022 Oct 21.

Abstract

An enantioselective three-component rearrangement of alkenylfurans with various cycloalkyl silyl peroxides and anilines has been developed by merging photoredox catalysis with chiral Brønsted acid catalysis. This protocol provides expedient access to a broad spectrum of ketoalkyl-functionalized 4-aminocyclopentenones in high yields with excellent enantio- and diastereoselectivities. Diverse functional groups can be introduced via facile product derivations.

摘要

通过将光氧化还原催化与手性布朗斯特酸催化相结合,开发了一种烯基呋喃与各种环烷基甲硅烷基过氧化物和苯胺的对映选择性三组分重排反应。该方法能以高收率、优异的对映选择性和非对映选择性方便地合成多种酮烷基官能化的4-氨基环戊烯酮。通过简便的产物衍生化可以引入多种官能团。

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