Convenient route to secondary sulfinates: application to the stereospecific synthesis of α-C-chiral sulfonamides.

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.