Investigation of the configurational stability of lithiated phosphine oxides using diastereomerically pure and enantiomerically enriched phosphine oxides

Abstract

Lithiation of racemic but diastereomerically pure phosphine oxides followed by electrophilic quench indicates that lithiated phosphine oxides are not configurationally stable over a period of minutes in THF at –78 °C. These results have been verified using an optically active phosphine oxide: lithiation and in situ quench experiments with Me₃SiCl and cyclobutanone indicate that the lithium derivatives are not configurationally stable even on the timescale of their reaction with these electrophiles.