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