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Wakchaure VN, Kaib PS, Leutzsch M, et al. Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines. Angew Chem Int Ed Engl. 2015;54(40):11852-6doi: 10.1002/anie.201504052.
Wakchaure, V. N., Kaib, P. S., Leutzsch, M., & List, B. (2015). Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines. Angewandte Chemie (International ed. in English), 54(40), 11852-6. https://doi.org/10.1002/anie.201504052
Wakchaure, Vijay N, et al. "Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines." Angewandte Chemie (International ed. in English) vol. 54,40 (2015): 11852-6. doi: https://doi.org/10.1002/anie.201504052
Wakchaure VN, Kaib PS, Leutzsch M, List B. Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines. Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11852-6. doi: 10.1002/anie.201504052. Epub 2015 Aug 14. PMID: 26382289.
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Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11852-6. doi: 10.1002/anie.201504052. Epub 2015 Aug 14.

Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines.

Angewandte Chemie (International ed. in English)

Vijay N Wakchaure, Philip S J Kaib, Markus Leutzsch, Benjamin List

Affiliations

  1. Max-Planck-Institut für Kohlenforschung, Kaiser -Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany).
  2. Max-Planck-Institut für Kohlenforschung, Kaiser -Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany). [email protected].

PMID: 26382289 DOI: 10.1002/anie.201504052

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.

Keywords: Brønsted acids; N-alkyl amines; disulfonimide; organocatalysis; reduction

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