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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: keith.fandrickboehringer-ingelheim.com

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 (free Supporting Information)


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Abstract

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