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Diphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
Author(s) -
Hayashi Yujiro,
Gotoh Hiroaki,
Hayashi Takaaki,
Shoji Mitsuru
Publication year - 2005
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.200500599
Subject(s) - silylation , yield (engineering) , michael reaction , trimethylsilyl , chemistry , silyl ether , organic chemistry , ether , catalysis , organocatalysis , enantioselective synthesis , materials science , metallurgy
The direct, catalytic, asymmetric Michael addition of aldehydes to nitroolefins in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme). The desired 1,4‐addition products were obtained in nearly optically pure form in good yield with high syn diastereoselectivity. TMS=trimethylsilyl.