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.fandrick
boehringer-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
ID: J54-Y2010-2380
