Tetrasubstituted pyrrolidines via a tandem aza-payne/hydroamination reaction

A mild tandem aza-Payne/hydroamination reaction of aziridinols mediated by dimethylsulfoxonium methylide is reported which yields highly functionalized pyrrolidine ring systems in one pot at room temperature. The resulting strained enamide products are potentially useful synthons for the rapid construction of densely substituted pyrrolidines and pyrrolidinones for use in natural product synthesis.