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Dynamic Kinetic Asymmetric Allylic Amination and Acyl Migration of Vinyl Aziridines with Imido Carboxylates
Author(s) -
Trost Barry M.,
Fandrick Daniel R.,
Brodmann Tobias,
Stiles Dylan T.
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.200700835
Subject(s) - amination , allylic rearrangement , kinetic resolution , vicinal , chemistry , reductive amination , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
An atom‐economical method has been developed for the preparation of chiral vicinal diamines through a dynamic kinetic asymmetric allylic amination and acyl‐group migration of vinyl aziridines with imido carboxylates. Application of the asymmetric transformation enabled the concise synthesis of the azepane core 1 of (+)‐balanol and its syn analogue.