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

C Wade Downey, Miles W Johnson, Kathryn J Tracy

Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, USA. wdowney@richmond.edu

The Journal of organic chemistry 2008 Apr 18

filter terms:

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.

Citation

C Wade Downey, Miles W Johnson, Kathryn J Tracy. One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf. The Journal of organic chemistry. 2008 Apr 18;73(8):3299-302