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Asymmetric Activation of tropos 2,2′‐Biphenol with Cinchonine Generates an Effective Catalyst for the Asymmetric Strecker Reaction of N ‐Tosyl‐Protected Aldimines and Ketoimines
Author(s) -
Wang Jun,
Hu Xiaolei,
Jiang Jun,
Gou Shaohua,
Huang Xiao,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2007
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.200703188
Subject(s) - aldimine , chemistry , strecker amino acid synthesis , catalysis , enantioselective synthesis , cinchonine , aryl , organic chemistry , alkyl , medicinal chemistry , combinatorial chemistry , stereochemistry
Tropo' bello! Asymmetric activation of tropos biphenol 1 and Ti(O i Pr) 4 with cinchonine 2 generates a remarkably effective catalyst in situ for the asymmetric Strecker reaction of N ‐tosyl (Ts) imines under mild conditions. Various substrates including aldimines, aryl alkyl ketoimines, and unsymmetrical diaryl ketoimines were investigated, and most of them exhibited high enantioselectivities (up to 99 % ee ) as well as high reactivities.