A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides.
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.
Andersen
N G
NG
Department of Chemistry, University of Calgary, Calgary, AB, Canada, T2N 1N4.
Ramsden
P D
PD
Che
D
D
Parvez
M
M
Keay
B A
BA