title: 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.
authors.affiliation: Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Wang
authors.forename: Jun
authors.initials: J
authors.lastname: Song
authors.forename: Ran
authors.initials: R
authors.lastname: Hong
authors.forename: Hongming
authors.initials: H
authors.lastname: Li
authors.forename: Li
authors.initials: L
authors.lastname: Deng
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D007097:Imines; D007211:Indoles