Approach to synthesis and structure of chiral multi-functionalized organophosphorus derivatives

Abstract

The diastereomerically pure organophosphorus derivatives containing multiple chiral centers 5 and 5′ were obtained, respectively, in 62%–84% yields with ≥98% de (diastereomeric excess) via asymmetric reaction of the chiron, 3-bromo-2(5H)-furanone 4 with racemic diethyl α-hydroxyl-substituted-phosphonates 3 + 3′ and further through the separation of the diastereomeric mixture by chromatography. The structures of the chiral organophosphorus derivatives were identified on the basis of their elementary and spectroscopic data, such as IR,1H NMR,13C NMR, MS and X-ray crystallography. In this report, the synthetic methods of the active organophosphorus substrates, the structure characterization and resolution, the optical purity and the stereo-chemistry of the chiral products were discussed. These results provide a new idea and a good method for synthesizing some natural organophosphorus compounds and approaching their biological activities, also a facile route to the application of organophosphorus substrates.