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Kinetic Resolution of Azomethine Imines by Brønsted Acid Catalyzed Enantioselective Reduction
Author(s) -
Bongers Amanda,
Moon Patrick J.,
Beauchemin André M.
Publication year - 2015
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.201507548
Subject(s) - enantioselective synthesis , kinetic resolution , chemistry , imine , catalysis , brønsted–lowry acid–base theory , azomethine ylide , enantiomer , combinatorial chemistry , stereochemistry , organic chemistry , cycloaddition , 1,3 dipolar cycloaddition
Azomethine imines are valuable substrates in asymmetric catalysis, and can be precursors to β‐amino carbonyl compounds and complex hydrazines. However, their utility is limited because complex and enantioenriched azomethine imines are often unavailable. Reported herein is a kinetic resolution of N,N′‐cyclic azomethine imines by enantioselective reduction ( s =13–43). This resolution was accomplished using a Brønsted acid catalyst, and represents the first example of the asymmetric reduction of azomethine imines. The pyrazolidinone product (up to 86 % ee ) and the recovered azomethine imine (up to 99 % ee ) can both be used to access the opposite enantiomers of valuable products.