Stereochemistry at the phosphorus atom during palladium-catalysed formation of carbon–phosphorous bonds and mechanistic implications

The reaction of (R)-(+)-isopropyl methylphosphinate (5) with bromobenene in the presence of Pd0 catalyst and triethylamine to afford (S)-(–)-isopropyl methylphenylphosphinate (6) proceeds with complete retention of configuration via a front-sided attack by phenylpalladium bromide on the phosphorus nucleophile.