Organolanthanide-Catalyzed Cyclization/Boration of 1,5- and 1,6-Dienes

Gary A. Molander* and Dirk Pfeiffer

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

G. A. Molander, D. Pfeiffer, Org. Lett., 2001, 3, 361-363.

DOI: 10.1021/ol006841s

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Abstract

1,5- and 1,6-Dienes undergo a cyclization/boration reaction in the presence of a catalytic amount of Cp*₂Sm·THF. The resulting organoboranes can be oxidized to the corresponding primary cyclic alcohols using standard conditions.

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proposed mechanism

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Key Words

cyclopentanes

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ID: J54-Y2001