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Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

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Wakchaure,  V.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Kaib,  Philip S.J.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wakchaure, V., Kaib, P. S., Leutzsch, M., & List, B. (2015). Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines. Angewandte Chemie International Edition, 54(40), 11852-11856. doi:10.1002/anie.201504052.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-EFDF-B
Abstract
A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2 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. 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.