Journal of Organic Chemistry 2008-04-18

One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf.

C Wade Downey, Miles W Johnson, Kathryn J Tracy

Index: J. Org. Chem. 73(8) , 3299-302, (2008)

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Abstract

Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are all effective substrates. The reaction proceeds in a single reaction flask, with no purification of the intermediate enol silane necessary.

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