Axis-to-Center Chirality Transfer Reactions of Phosphates with a Binaphthyl Group and Their Congeners: New Synthetic Routes to P-Chirogenic Organophosphorus Compounds

Abstract

Abstract Novel synthetic methods for P-chirogenic four-coordinate pentadentate organophosphorus compounds are described. The synthetic pathways commenced with the use of phosphates bearing a binaphthyl group and their congeners. These compounds underwent reactions with fluoride ion, metal hydroxides, metal alkoxides, and Grignard reagents, resulting in the transfer of axial chirality from the binaphthyl group to the central chirality of the phosphorus atom. As a result, P-chirogenic products incorporating a binaphthyl group were obtained. The substitution reactions of these newly formed products with metal alkoxides and Grignard reagents led to the formation of P-chirogenic phosphates, phosphonates, phosphinates, and some sulfur isologues.