P-Stereogenic Phosphorus Compounds: Effect of Aryl Substituents on the Oxidation of Arylmethylphenylphosphanes under Asymmetric Appel Conditions

The effects of aryl ring substitution on the dynamic resolution of aryl(methyl)phenylphosphanes under asymmetric Appel reaction conditions have been studied. As expected, substitution at the ortho position strongly affects the degree of stereoselection that can be achieved. Unexpectedly, however, there was no variation of stereoselectivity with the electronic nature of the para substituents, which suggests that there are two selection processes in operation. An unusual halogen-exchange process was observed in the arylphenylphosphinous chlorides on route to the required tertiary phosphane substrates.