Organocatalytic Asymmetric Vinylogous Michael Addition of Electron-Deficient Aryl Alkane Nucleophiles to Enals

We report herein a protocol for an organocatalyzed asymmetric vinylogous Michael addition of aryl alkane nucleophiles with enals under base- and additive-free conditions. A series of allylic building blocks were obtained in 60%–93% yield and 88–99% ee with 20 mol % diphenylprolinol silyl ether as ca...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-12, Vol.88 (24), p.16773-16782
Main Authors: Zhang, Zhiguang, Sui, Ao, Zhang, Xiaomin, Wang, Xu, He, Xinyi, Zhang, Bingzhu, Wu, Haixia
Format: Article
Language:English
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Summary:We report herein a protocol for an organocatalyzed asymmetric vinylogous Michael addition of aryl alkane nucleophiles with enals under base- and additive-free conditions. A series of allylic building blocks were obtained in 60%–93% yield and 88–99% ee with 20 mol % diphenylprolinol silyl ether as catalyst. This protocol has advantages such as excellent chemoselectivity and regioselectivity, good tolerance of functionalities, and simple reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01232