A series of side-chain polyacrylates containing chiral, optically active sulfoxide substituents was prepared by the enantioselective oxidation of the corresponding prochiral polyacrylates containing prochiral sulfide substituents. A chiral sulfonyloxaziridine was used as the oxidant. The chemical modification was selective from chemical and stereochemical standpoints. The resulting polymers formed chiral nematic and/or smectic phases with a slightly decreased propensity to give stable and persistent mesophases with respect to the parent sulfide containing polymers.