Copper-Catalyzed Dynamic Kinetic Resolution of Secondary Phosphine Oxides

Copper-catalyzed dynamic kinetic resolution of secondary phosphine oxides has been successfully developed, providing a general method for the gram-scale enantioselective synthesis of P-stereogenic cyclic phosphine oxides with high yields and high enantioselectivities. The products could be easily reduced to the corresponding useful P(III)-stereogenic cyclic phosphines. A mechanism of the dynamic kinetic resolution involving the unusual rapid racemization of SPOs has been proposed.

Automated summary

A general method for the gram-scale enantioselective synthesis of P-stereogenic cyclic phosphine oxides has been developed using copper-catalyzed dynamic kinetic resolution, leading to high yields and high enantioselectivities. The resulting products can be easily reduced to obtain useful P(III)-stereogenic cyclic phosphines. A proposed mechanism involves the unusual rapid racemization of SPOs.