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A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides
N G Andersen1, P D Ramsden, D Che
1Department of Chemistry, University of Calgary, Calgary, AB, Canada, T2N 1N4.
The Journal of Organic Chemistry
|October 30, 2001
Abstract:
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.