Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 40, Pages 11852-11856Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504052
Keywords
Bronsted acids; disulfonimide; N-alkyl amines; organocatalysis; reduction
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Funding
- Max-Planck-Society
- European Research Council (Advanced Grant High Performance Lewis Acid Organocatalysis, HIPOCAT)
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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.
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