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Catalytic Asymmetric Michael Reactions of Acetaldehyde
Author(s) -
GarcíaGarcía Patricia,
Ladépêche Arnaud,
Halder Rajkumar,
List Benjamin
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.200800847
Subject(s) - acetaldehyde , enantiopure drug , michael reaction , trimethylsilyl , pyrrolidine , catalysis , chemistry , silylation , organic chemistry , derivative (finance) , enantioselective synthesis , ethanol , economics , financial economics
Acetaldehyde, now a big contender : A silyl prolinol derivative was found to catalyze the first Michael addition of acetaldehyde with both aromatic and aliphatic nitroolefins in excellent enantioselectivities (see scheme, TMS=trimethylsilyl). The utility of the reaction is illustrated in the synthesis of three current pharmaceuticals and in the synthesis of an enantiopure 3‐monosubstituted pyrrolidine.