Metal Effects on the Asymmetric Cycloaddition Reactionbetween 3,4-Dimethyl-1-phenylphosphole and Sulfoxide.

Theorthometalated [1-(dimethylamino)ethyl]naphthalene platinum(II) complexhas been used successfully to promote the asymmetric cycloadditionreaction between 3,4-dimethyl-1-phenylphosphole and sulfoxide in highselectivity. The exo-cycloadduct coordinated to theplatinum template as bidentate chelates via their phosphorus and sulfuratoms. The dichloro platinum complexes could be crystallized and werestable in the solid state as well as in solution. Optically pure P–Sbidentate ligands could be liberated from these dichloro complexesby treatment with aqueous potassium cyanide. The study also highlightsthe difference in reactivity and mode of substrate activation betweenan earlier study involving a Pd analogue of the template and the currentresults. [ABSTRACT FROM AUTHOR]