Enantioselective Brønsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines

Org Lett. 2005 Aug 18;7(17):3781-3. doi: 10.1021/ol0515964.

Abstract

The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst. [reaction: see text]