Asymmetric Organocatalytic Conjugate Addition of Thiocarboxylic Acids to In Situ‐Generated ortho‐Quinomethanes in Oil‐Water Phases

An asymmetric conjugate addition of thiocarboxylic acids to in situ‐generated ortho‐quinomethanes (o‐QMs) catalyzed by bifunctional squaramide catalysts has been developed. The transformation proceeds with high yields (up to 96%) and enantioselectivities (up to 96% ee) in the oil‐water phases. The r...

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Bibliographic Details
Published in:	Advanced synthesis & catalysis Vol. 359; no. 23; pp. 4170 - 4176
Main Authors:	Wang, Yifeng, Chu, Mingming, Zhang, Cheng, Shao, Juanjuan, Qi, Suosuo, Wang, Biao, Du, Xiaohua, Xu, Danqian
Format:	Journal Article
Language:	English
Published:	Heidelberg Wiley Subscription Services, Inc 11-12-2017
Subjects:	asymmetric catalysis Catalysis conjugate addition oil-water phases ortho-quinomethanes thiocarboxylic acids
Online Access:	Get full text
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Summary:	An asymmetric conjugate addition of thiocarboxylic acids to in situ‐generated ortho‐quinomethanes (o‐QMs) catalyzed by bifunctional squaramide catalysts has been developed. The transformation proceeds with high yields (up to 96%) and enantioselectivities (up to 96% ee) in the oil‐water phases. The resulting thioester could be converted facilely into the chiral benzyl mercaptan in high yield without loss of enantioselectivity. The study also showed that the oil‐water biphase contributed significantly to the efficiency of the catalytic system.
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.201700825