Tetrahedron letters

A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf

CW Downey, MW Johnson

Index: Downey, C. Wade; Johnson, Miles W. Tetrahedron Letters, 2007 , vol. 48, # 20 p. 3559 - 3562

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Citation Number: 35

Abstract

A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation- Mukaiyama aldol reaction in the presence of Hunig's base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75–97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for full conversion.

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