Hydrolysis of optically active cis-[Ru(bpy)(2)(py)Cl]-(PF6) yields cis-[Ru(bpy)(2)(py)(H2O)](ClO4)(2) with 80% retention of configuration. The oxidation to cis-[Ru(bpy)(2)(py)(O)](ClO4)(2) is also found to involve retention of the absolute configuration. This optically active oxidant is slow to racemize and has been characterized by circular dichroism spectroscopy. Asymmetric oxidation of a prochiral methyl p-tolyl sulfide to a chiral sulfoxide by the chiral oxidant complex is observed with 30% ee in a water-acetonitrile mixture.