Organic Chemistry Portal



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:

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

DOI: 10.1021/jo901513v


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.

see article for more examples

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