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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

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

Wang Yong-Qiang YQ Song Jun J Hong Ran R Li Hongming H Deng Li L

Journal of the American Chemical Society 20060601 25

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 met ...[more]

PMID: 16787078

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