DOI
10.1021/jo100828c
Abstract
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.
Document Type
Article
Publication Date
8-6-2010
Publisher Statement
Copyright © 2010, American Chemistry Society. This article first appeared in Journal of Organic Chemistry: 75:15 (2010), 5351-5354.
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Recommended Citation
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.
