Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst.

ABSTRACT: In this communication, we report an asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst. This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines. This reaction is operationally simple and, unprecedentedly, affords high enantioselectivity for a wide range of indoles and both aryl and alkyl imines. This establishes a direct, convergent, and versatile approach to optically active 3-indolyl methanamines, a structural motif embedded in numerous indole alkaloids and synthetic indole derivatives.

SUBMITTER: Wang YQ 

PROVIDER: S-EPMC3161403 | biostudies-literature | 2006 Jun

REPOSITORIES: biostudies-literature