α-Tolylsulfinylation of Ketones via Their Trimethylsilyl Enol Ethers. One-Step Synthesis of β-Ketosulfoxides

Abstract

Ketones are reported to be conveniently converted into their α-tolylsulfinylated derivatives. This new procedure is based on the reaction of their corresponding trimethylsilyl enol ethers with p-toluenesulfinyl p-tolylsulfone in the presence of tris(dimethylamino)sulfur trimethylsilyldifluoride (TAS-F). Considering that β-ketosulfoxides are key intermediates for the preparation of α,β-unsaturated ketones, this procedure turns out to be of rather broad synthetic relevance.