Convenient Route to Secondary Sulfinates: Application to the Stereospecific Synthesis of α-<i>C</i>-Chiral Sulfonamides

Abstract

A convenient synthesis of α-chiral sulfinates from readily available precursors has been accomplished via the corresponding heterocyclic thioethers and sulfones. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides α-C-chiral primary sulfonamides in good yield (14 examples) with retention of stereochemical purity.