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Boron-Catalyzed Direct Aldol Reactions of Pyruvic Acids

Doris Lee, Stephen G. Newman and Mark S. Taylor*

*Department of Chemistry, Lash Miller Laboratories, University of Toronto 80 St. George Street, Toronto ON M5S 3H6, Canada, Email: mtaylorchem.utoronto.ca

D. Lee, S. G. Newman, M. S. Taylor, Org. Lett., 2009, 11, 5486-5489.

DOI: 10.1021/ol902322r (free Supporting Information)


Abstract

A boron-catalyzed aldol reaction of pyruvic acids with aldehydes in water at room temperature delivers useful isotetronic acid derivatives in high yields. Both boronic and borinic acids function as catalysts, with the latter demonstrating particularly high activity. A wide range of aldehydes, including enolizable species, may be employed.

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Key Words

Butenolides


ID: J54-Y2009-3490