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

Steven M. Raders and John G. Verkade*

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

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

DOI: 10.1021/jo901571y

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Abstract

The Mukayiama aldol reaction of aldehydes is efficiently catalyzed by a dimeric alumatrane complex at mild or subambient temperatures. The protocol tolerates a wide variety of electron-rich, neutral, and deficient aryl, alkyl, and heterocyclic aldehydes. A wide variety of enol silyl ethers are also tolerated.

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

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

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Key Words

Mukaiyama Aldol Addition, β-Hydroxy Esters

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ID: J42-Y2009-2260