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One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf

C. Wade Downey,* Miles W. Johnson and Kathryn J. Tracy

*Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, Email: wdowneyrichmond.edu

C. W. Downey, M. W. Johnson, K. J. Tracy, J. Org. Chem., 2008, 73, 3299-3302.

DOI: 10.1021/jo8001084 (free Supporting Information)


Abstract

Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base in a single reaction flask, without purification of the intermediate enol silane. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates.

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Key Words

Mukaiyama Aldol Addition, β-hydroxy ketones, β-hydroxy carboxylic acid derivatives


ID: J42-Y2008-1080