Addition of carbon nucleophiles to cyclic N-tosyliminium ions, derived from α-hydroxy and α- methoxy tosylamides (5a, b and 6a, b, respectively) is described. In general, good to excellent yields were obtained when allytrimethylsilane, 1-tbutyldimethylsilyloxy-1- ethoxyethane, and trimethylsilyl cyanide were used as nucleophiles.