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A General Catalyst for the Asymmetric Strecker Reaction
Author(s) -
Sigman Matthew S.,
Vachal Petr,
Jacobsen Eric N.
Publication year - 2000
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/(sici)1521-3773(20000403)39:7<1279::aid-anie1279>3.0.co;2-u
Subject(s) - strecker amino acid synthesis , imine , catalysis , enantioselective synthesis , yield (engineering) , chemistry , aldimine , organic chemistry , combinatorial chemistry , materials science , metallurgy
From a parallel library of 70 compounds , the salicylidene imine derivative 1 was identified as a remarkably enantioselective and general catalyst for the Strecker reaction with a variety of aromatic and aliphatic aldimines. While the soluble catalyst affords slightly higher ee values in most reactions, the use of its polystyrene‐resin‐bound analogue allows facile isolation of the Strecker products in nearly quantitative yield, and it can be recycled over ten times without loss of activity or selectivity.