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Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate

C. Wade Downey*, Miles W. Johnson, Daniel H. Lawrence, Alan S. Fleisher and Kathryn J. Tracy

*Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, Email:

C. W. Downey, M. W. Johnson, D. H. Lawrence, A. S. Fleisher, K. J. Tracy, J. Org. Chem., 2010, 75, 5351-5354.

DOI: 10.1021/jo100828c

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In the presence of TMSOTf and a trialkylamine base, acetic acid or TMSOAc undergo aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. The reaction appears to proceed via trimethylsilyl ester formation, bis-silyl ketene acetal formation, and TMSOTf-catalyzed Mukaiyama aldol addition.

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proposed reaction pathway

Key Words

Mukaiyama aldol addition, β-hydroxy carboxylic acids

ID: J42-Y2010-2210