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Organocatalyzed Asymmetric Vinylogous Michael Reactions of 3,5‐Dialkyl‐Substituted 4‐Nitroisoxazoles: A Direct Method for the Synthesis of Chiral Isoxazole Derivatives
Author(s) -
Zhang Yong,
Wei Biaowen,
Lin Hui,
Cui Weirong,
Zeng Xianqiang,
Fan Xiaolin
Publication year - 2015
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.201400833
Subject(s) - chemistry , isoxazole , organocatalysis , michael reaction , organic chemistry , catalysis , enantioselective synthesis , combinatorial chemistry
The direct asymmetric vinylogous Michael addition of 3,5‐dialkyl‐substituted 4‐nitroisoxazoles with α,β‐unsaturated aldehydes catalyzed by a diphenylprolinol TBS ether organocatalyst is described, giving products with moderate to good yields and up to excellent enantioselectivities (96% ee ). This approach provides an easy access to highly functionalized chiral isoxazole derivatives.