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Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

Daniel R. Fandrick*, Keith R. Fandrick, Jonathan T. Reeves, Zhulin Tan, Courtney S. Johnson, Heewon Lee, Jinhua J. Song, Nathan K. Yee and Chris H. Senanayake

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

D. R. Fandrick, K. R. Fandrick, J. T. Reeves, Z. Tan, C. S. Johnson, H. Lee, J. J. Song, N. K. Yee, C. H. Senanayake, Org. Lett., 2010, 12, 88-91.

DOI: 10.1021/ol902457m (free Supporting Information)



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Abstract

A propargylation of aldehydes and ketones with allenyl and propargyl boronates is mediated by a catalytic amount of zinc. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

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Key Words

Homopropargylic Alcohols


ID: J54-Y2010-0110