Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate

被引：28

作者：

Downey, C. Wade ^{[1
]}

Johnson, Miles W. ^{[1
]}

Lawrence, Daniel H. ^{[1
]}

Fleisher, Alan S. ^{[1
]}

Tracy, Kathryn J. ^{[1
]}

机构：

[1] Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 15期

关键词：

ESTER; BORON; RING;

D O I：

10.1021/jo100828c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5351 / 5354

页数：4

共 17 条

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