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Asymmetric Organocatalytic Cascade Michael/Michael/Henry Reaction Sequence: Control of All Stereocenters in One Cyclohexane Skeleton
Author(s) -
Mao Zhifeng,
Jia Yaomei,
Xu Zhaoqing,
Wang Rui
Publication year - 2012
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.201200008
Subject(s) - michael reaction , stereocenter , chemistry , enantioselective synthesis , cascade , thiourea , nitroaldol reaction , cyclohexane , organocatalysis , cascade reaction , squaramide , organic chemistry , yield (engineering) , catalysis , chromatography , materials science , metallurgy
The highly diastereo‐ and enantioselective relay cascade Michael/Michael/Henry reaction catalyzed by combination of readily available diphenylprolinol silyl ether and the quinine thiourea in a one‐pot fashion has been developed. Up to 70% yield and up to >99% enantioselectivity of the single major isomer were obtained from the cascade reactions.