N-Heterocyclic Carbene-Catalyzed Mukaiyama Aldol Reactions

Jinhua J. Song,* Zhulin Tan, Jonathan T. Reeves, 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
Org. Lett., 2007, 9 (6), pp 1013–1016
DOI: 10.1021/ol0630494
Publication Date (Web): February 13, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jsong@rdg.boehringer-ingelheim.com

Abstract

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N-Heterocyclic carbenes were shown to be highly effective catalysts to promote Mukaiyama aldol reactions. In the presence of only 0.5 mol % of N-heterocyclic carbene (5), various aldehydes and 2,2,2-trifluoroacetophenone underwent Mukaiyama aldol reactions in THF with trimethylsilyl ketene acetal (2) at 23 °C as well as with trimethylsilyl enol ether (7) at 0 °C to afford aldol adducts in good yields. These conditions are extremely mild and operationally simple and tolerate various functional groups.

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History

  • Published In Issue March 15, 2007
  • Received December 17, 2006

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