Synthesis of P-stereogenic phosphinates via an axis-to-center chirality transfer by the reaction of phosphonates having a binaphthyloxy group with Grignard reagents

Abstract

The reactions of phosphonates having a binaphthyloxy group with Grignard reagents gave the corresponding P-stereogenic phosphinates in good to high yields with high diastereoselectivity. In this reaction, an axis-to-center chirality transfer from a binaphthyl group to the resulting phosphorus atom took place stereospecifically. Both diastereomers with opposite configurations could be obtained by changing the combination of carbon-containing functional groups on the phosphorus atom and the Grignard reagents.