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Disulfonimide‐Catalyzed Asymmetric Reduction of N ‐Alkyl Imines
Author(s) -
Wakchaure Vijay N.,
Kaib Philip S. J.,
Leutzsch Markus,
List Benjamin
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.201504052
Subject(s) - alkyl , chemistry , catalysis , hydrochloride , organic chemistry , combinatorial chemistry , medicinal chemistry
A chiral disulfonimide (DSI)‐catalyzed asymmetric reduction of N ‐alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc 2 O has been developed. The reaction delivers Boc‐protected N ‐alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross‐coupling of ketones with diverse amines, and it was applied in the synthesis of the pharmaceuticals ( S )‐Rivastigmine, NPS R‐568 Hydrochloride, and ( R )‐Fendiline.