A Facile and Efficient Direct Aldol Addition of Simple Thioesters

Julianne M. Yost, Guoqiang Zhou and Don M. Coltart*

*Department of Chemistry, Duke University, Durham, North Carolina 27708, Email: don.coltartduke.edu

J. M. Yost, G. Zhou, D. M. Coltart, Org. Lett., 2006, 8, 1503-1506.

DOI: 10.1021/ol060413q

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Abstract

Simple thioesters undergo direct aldol addition to aldehydes in the presence of a Lewis acid and i-Pr₂NEt. The reactions proceed extremely rapidly and in excellent yield.

see article for more examples

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Direct Carbon-Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002

G. Zhou, D. Lim, D. M. Coltart, Org. Lett., 2008, 10, 3809-3812.

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Key Words

Aldol Addition, Thioesters, β-Hydroxy Carboxylic Compounds

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ID: J54-Y2006-920