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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, Email: jsongrdg.boehringer-ingelheim.com

J. J. Song, Z. Tan, J. T. Reeves, N. K. Yee, C. H. Senanayake, Org. Lett., 2007, 9, 1013-1016.

DOI: 10.1021/ol0630494 (free Supporting Information)


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Abstract

In the presence of only 0.5 mol % of an N-heterocyclic carbene, various aldehydes and 2,2,2-trifluoroacetophenone underwent Mukaiyama aldol reactions in THF with a trimethylsilyl ketene acetal as well as with a trimethylsilyl enol ether to afford aldol adducts in good yields. These conditions are extremely mild and operationally simple and tolerate various functional groups.

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Key Words

Mukaiyama Aldol Addition, β-Hydroxyesters, β-Hydroxyketones, Organocatalysis


ID: J54-Y2007-0860