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Paper | Regular issue | Vol 32, No. 11, 1991, pp.2105-2110
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5745
Use of 2D Nmr for the Assignment of Structure of 1,3,2-oxazaphospholidin-2-ones

Camille A. Boulet,* Scott J. Tregear, and Arnold S. Hansen

*Defence Research Establishement Suffield, P.O. Box 4000, Medicine Hat, Alberta T1A 8K6, Canada

Abstract

Reaction of a chiral amino alcohol with an alkyl phosphorodichloridate gives a mixture of diastereomeric 1,3,2-oxazaphospholidin-2-ones which are epimeric at phosphrous. Analysis by 1D and 2D nmr has shown that it is possible to establish the absolute configuration at phosphorus by nmr techniques. Specifically, stereospecific differences in chemical shifts and NOESY spectra for each isomer are used to establish the absolute stereochemistry at phosphorus for (4R,5S)-2-ethoxy-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one diasteremers.