High stereoselectivity in chelation-controlled intermolecular Heck reactions with aryl chlorides, vinyl chlorides and vinyl triflates.

Org Biomol Chem

Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, BMC, Uppsala, Box 574, SE-751 23, Sweden.

Published: February 2008

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Article Abstract

Highly stereoselective chelation-controlled Pd(0)-catalyzed beta-arylations and beta-vinylations of a five-membered chiral, pyrrolidine-based vinyl ether were achieved using aryl- and vinyl chlorides as substrates, yielding quaternary 2-aryl/vinyl-2-methyl cyclopentanones in 89-96% ee under neutral reaction conditions.

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http://dx.doi.org/10.1039/b719131fDOI Listing

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