Metal-catalyzed oxidation and epoxidation of α-hydroxy vinyl and dienyl sulfoxides

Formula chem. Treatment of acyclic α-hydroxyalkyl α,β-unsaturated sulfoxides with t-BuOOHNO(acac) 2 results in rapid oxidation to the unsaturated sulfones followed by an unusual regio- and stereoselective epoxidation at the unsaturated sulfones; this methodology has been applied to the preparation of carbohydrate-like fragments.