α-Tolylsulfinylation of ketones via their trimethylsilyl enol ethers. One step synthesis of β-ketosulfoxides R. Caputo; C. Ferreri; L. Longobardo; G. Palumbo; S. Pedatella

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.