Highly Stereoselective Route to Dialkyl Sulfoxides Based upon the Sequential Displacement of Oxygen and Carbon Leaving Groups by Grignard Reagents on Sulfinyl Compoundss

Menthyl (S)-p-bromobenzenesulfinate was prepared and subjected to two different substitution reactions with Grignard reagents. Enantiopure dialkyl sulfoxides were quickly obtained with this conceptually straightforward and experimentally simple procedure.