Kinetic resolution of P-chiral tertiary phosphines and chlorophosphines: a new approach to optically active phosphoryl and thiophosphoryl compounds

Treatment of racemic P-stereogenic tertiary phosphines with enantiomerically pure bis-phosphoryl and bis-thiophosphoryl disulfides under kinetic resolution conditions (2:1 ratio) afforded enantiomerically enriched tertiary phosphine oxides or phosphine sulfides with ee values up to 39%. In a similar way from racemic tert-butylphenylchlorophosphine, optically active tert-butylphenylphosphinoyl chloride with 50% ee was obtained. The same reaction performed under dynamic kinetic resolution conditions (1:1 ratio of reagents) in the presence of chloride ions gave phosphinoyl chloride with 70% ee.