Dynamic Kinetic Asymmetric Allylic Amination and Acyl Migration of Vinyl Aziridines with Imido Carboxylates | Zendy

Trost Barry M. | Zendy; Fandrick Daniel R. | Zendy; Brodmann Tobias | Zendy; Stiles Dylan T. | Zendy

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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.

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