In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. The reaction appears to proceed via a three-step, one-pot process, including in situ trimethylsilyl ester formation, bis-silyl ketene acetal formation, and TMSOTf-catalyzed Mukaiyama aldol addition. Independently synthesized TMSOAc also undergoes aldol additions under similar conditions.
Copyright © 2010, American Chemistry Society. This article first appeared in Journal of Organic Chemistry: 75:15 (2010), 5351-5354.
Please note that downloads of the article are for private/personal use only.
Johnson, C. Wade, Miles W. Johnson, Daniel H. Lawrence, Alan S. Fleisher, and Kathryn J. Tracy. "Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate." Journal of Organic Chemistry 75, no. 15 (August 6, 2010): 5351-354. doi:10.1021/jo100828c.