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Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether
Author(s) -
Hayashi Yujiro,
Itoh Takahiko,
Ohkubo Masahiro,
Ishikawa Hayato
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801130
Subject(s) - acetaldehyde , chemistry , silylation , catalysis , nitro , michael reaction , organic chemistry , ether , trimethylsilyl , ethanol , alkyl
An acetaldehyde breakthrough : The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS=trimethylsilyl). The desired 1,4‐addition products, α‐unsubstituted γ‐nitro aldehydes, were obtained in good yields with excellent enantioselectivities.