A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides

Article abstract of DOI:10.1021/jo015909u

The resolution of a variety of (±)-P-stereogenic phosphines is achieved by exploiting the Staudinger reaction of a (±)-phosphine with enantiopure (1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonyl azide. The resulting mixtures of diastereomeric phosphinimines are generally separable by fractional crystallization or flash chromatography. Subsequent acid-catalyzed hydrolysis provides the corresponding optically pure phosphine oxides in high yields.