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.
Copyright © 2008, American Chemistry Society. This article first appeared in Journal of Organic Chemistry: 73:8 (2008), 3299-3302.
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Downey, C. Wade, Miles W. Johnson, and Kathryn J. Tracy. "One-Pot Enol Silane Formation-Mukaiyama Aldol-Type Addition to Dimethyl Acetals Mediated by TMSOTf." Journal of Organic Chemistry 73, no. 8 (April 18, 2008): 3299-302. doi:10.1021/jo8001084.