Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst.
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.
Wang
Yong-Qiang
YQ
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Song
Jun
J
Hong
Ran
R
Li
Hongming
H
Deng
Li
L
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D007097:Imines; D007211:Indoles