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N-Heterocyclic Carbene-Catalyzed Silyl Enol Ether Formation

Jinhua J. Song,* Zhulin Tan, Jonathan T. Reeves, Daniel R. Fandrick, 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: jeff.songboehringer-ingelheim.com

J. J. Song, Z. Tan, J. T. Reeves, D. R. Fandrick, N. K. Yee, C. H. Senanayake, Org. Lett., 2008, 10, 877-880.

DOI: 10.1021/ol703025b


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Abstract

N-Heterocyclic carbenes (NHCs) catalyze the silyl transfer from trialkylsilyl ketene acetals to ketones. A series of enolizable ketones as well as cyclohexanecarboxaldehyde were efficiently converted into the corresponding silyl enol ethers at 23°C in THF.

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Key Words

Silyl Enol Ethers, Organocatalysis


ID: J54-Y2008-0600