Two-Step Transesterification of Phosphates, Phosphorothioates, and Phosphonates with a Binaphthyl Group for the Synthesis of P-Chirogenic Phosphates and Phosphonates

Abstract Two-step transesterification of four-coordinate pentavalent organophosphorus compounds with a binaphthyl group has been studied in detail. The first step involves transfer of the axial chirality of a ­hydroxybinaphthyl group to the central chirality of the phosphorus atom. The second step is the substitution reaction of P-chirogenic compounds with a hydroxybinaphthyl group with lithium alkoxides, leading to the formation of P-chirogenic phosphates and phosphonates with primary and secondary alkoxy groups.