A novel solid-phase strategy allows the efficient preparation of "traceless" sulfahydantoins. A total of 28 derivatives, with crude purity generally higher than 85%, were prepared by parallel synthesis. Through reductive alkylations, Mitsunobu reactions, and sulfamoylation reactions on oxime resin, the synthetic strategy affords sulfahydantoin derivatives selectively substituted at N(2), N(5) and N(2), N(5) positions, although yields of disubstituted compounds are lower. The mild reaction conditions involved lead to sulfahydantoins without racemization.