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Asymmetric Organocatalytic Conjugate Addition of Thiocarboxylic Acids to In Situ‐Generated ortho ‐Quinomethanes in Oil‐Water Phases
Author(s) -
Wang Yifeng,
Chu Mingming,
Zhang Cheng,
Shao Juanjuan,
Qi Suosuo,
Wang Biao,
Du Xiaohua,
Xu Danqian
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700825
Subject(s) - chemistry , bifunctional , conjugate , squaramide , catalysis , yield (engineering) , enantioselective synthesis , thioester , in situ , organic chemistry , medicinal chemistry , organocatalysis , metallurgy , mathematical analysis , materials science , mathematics , enzyme
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.