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Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

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

Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11852-6.

PMID: 26382289

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP135273744	R-568 hydrochloride		135273-74-4	Price

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