STEREOSPECIFIC SYNTHESIS OF P-EPIMERIC (RP1, RP2)-BIS-[O-L-MENTHYLPHENYLPHOSPHONOTHIONYL] DISELENIDE - A NEW VARIANT OF THE STEREOSELECTIVESTAUDINGER REACTION

An efficient procedure is described that leads to pure (S-p)-O-1-menth ylphenylthiophosphinate. The absolute configuration of this diastereom er was assigned by chemical correlation and confirmed by X-ray crystal lography. The reaction of the isomer with phenyl azide, leading to ami date, is a new variant of the stereoselective Staudinger reaction. Add ition of elemental selenium to the (S-p)-thiophosphinate led to diaste reomeric O-1-menthylphenylselenophosphonothioic acid, which was finall y oxidized to the diastereomeric (p)1,R(p)2)-bis[O-1-menthylphenylphos phonothionyl] diselenide. The diselenide structure was unambiguously c onfirmed by P-31 NMR spectroscopy.