Regioselective synthesis of N-substituted-4-substituted isothiazolidine-1,1-dioxides

A novel and efficient synthesis of a range of racemic and enantioenriched N-substituted-4-substituted isothiazolidine-1,1-dioxides from epoxides and sulfonamides is described. The critical choice of the activating group for the cyclization event is discussed. The application of this methodology to the synthesis of N-substituted-4,5-disubstituted derivatives is also described.