期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 15, 页码 5351-5354出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo100828c
关键词
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资金
- Research Corporation
- Thomas F. Jeffress and Kate Miller Jeffress Memorial Trust
- University of Richmond Department of Chemistry
- University of Richmond College of Arts and Sciences
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 beta-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.
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