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Kinetic Resolution of 1,2‐Diamines via Organocatalyzed Asymmetric Electrophilic Aminations of Anilines

Kinetic Resolution of 1,2‐Diamines via Organocatalyzed Asymmetric Electrophilic Aminations of... An efficient kinetic resolution (KR) protocol for 1,2‐diamines has been developed through asymmetric electrophilic aminations of anilines enabled by chiral phosphoric acid catalysis. A wide array of substituted 1,2‐diamines were compatible with this method, generating both the recovered staring materials and the amination products with high enantioselectivities (with s‐factor up to 218). Notably, this method is amenable to the kinetic resolution of 1,2‐diamines bearing α‐tertiary amine moieties, which represents the first KR of this type of 1,2‐diamines. Facile removal of the introduced hydrazine group and oxidative cleavage of the N‐aryl group to release the free primary amine demonstrate the value of this method. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

Kinetic Resolution of 1,2‐Diamines via Organocatalyzed Asymmetric Electrophilic Aminations of Anilines

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Publisher
Wiley
Copyright
© 2022 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH
eISSN
1614-7065
DOI
10.1002/cjoc.202200125
Publisher site
See Article on Publisher Site

Abstract

An efficient kinetic resolution (KR) protocol for 1,2‐diamines has been developed through asymmetric electrophilic aminations of anilines enabled by chiral phosphoric acid catalysis. A wide array of substituted 1,2‐diamines were compatible with this method, generating both the recovered staring materials and the amination products with high enantioselectivities (with s‐factor up to 218). Notably, this method is amenable to the kinetic resolution of 1,2‐diamines bearing α‐tertiary amine moieties, which represents the first KR of this type of 1,2‐diamines. Facile removal of the introduced hydrazine group and oxidative cleavage of the N‐aryl group to release the free primary amine demonstrate the value of this method.

Journal

Chinese Journal of ChemistryWiley

Published: Jul 15, 2022

Keywords: Asymmetric catalysis; 1,2‐Diamines; Kinetic resolution; Chiral phosphoric acids; Amination

References