Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2015 Sep 19

PMID 26382289

Citations 18

Authors

Vijay N Wakchaure

Philip S J Kaib

Markus Leutzsch

Benjamin List

Affiliations

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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.

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