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Mild and General Zinc-Alkoxide-Catalyzed Allylations of Ketones with Allyl Pinacol Boronates

Keith R. Fandrick*, Daniel R. Fandrick, Joe J. Gao, Jonathan T. Reeves, Zhulin Tan, Wenjie Li, Jinhua J. Song, Bruce Lu, Nathan K. Yee and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, Email:

K. R. Fandrick, D. R. Fandrick, J. J. Gao, J. T. Reeves, Z. Tan, W. Li, J. J. Song, B. Lu, N. K. Yee, C. H. Senanayake, Org. Lett., 2010, 12, 3748-3751.

DOI: 10.1021/ol101301s

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A general allylation of a diverse array of ketones with allyl boronates is effective with 2 mol % of a zinc alkoxide catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.

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Key Words

Homoallylic Alcohols

ID: J54-Y2010-2380