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P(PhCH2NCH2CH2)3N Catalysis of Mukaiyama Aldol Reactions of Aliphatic, Aromatic, and Heterocyclic Aldehydes and Trifluoromethyl Phenyl Ketone

Venkat Reddy Chintareddy, Kuldeep Wadhwa and John G. Verkade*

*Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, Email: jverkadeiastate.edu

V. R. Chintareddy, K. Wadhwa, J. G. Verkade, J. Org. Chem., 2009, 74, 8118-8132.

DOI: 10.1021/jo901513v (free Supporting Information)


Abstract

A proazaphosphatrane is a very efficient catalyst for Mukaiyama aldol reactions of aldehydes with trimethylsilyl enolates in THF solvent. The reaction conditions are mild and operationally simple, and a variety of aryl functional groups, such as nitro, amino, ester, chloro, trifluorometh yl, bromo, iodo, cyano, and fluoro groups, are tolerated.

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Catalysis of Mukaiyama Aldol Reactions by a Tricyclic Aluminum Alkoxide Lewis Acid

S. M. Raders, J. G. Verkade, J. Org. Chem., 2009, 74, 5417-5428.


Key Words

Mukaiyama Aldol Addition, β-Hydroxy Esters, β-Hydroxy Ketones, Enones, Organocatalysis


ID: J42-Y2009-3150