Ab. Ouryupin et al., CHIRAL DISCRIMINATION IN NONRACEMIC MIXTURES OF METHANEPHOSPHONIC ACID, N,N'-BIS(1-PHENYLETHYL)DIAMIDES, Chirality, 6(1), 1994, pp. 1-4
Enantiomeric (S, S)- and (R,R)-bis(1-phenylethyl)diamidomethylphosphon
ates, the phosphorus atom being prochiral, have been synthesized, star
ting from the methanephosphonic acid dichloride and corresponding chir
al amines. The splitting observed in the P-31-NMR spectra of their non
racemic mixtures may be accounted for the self-discrimination of chira
l species. This effect can be very useful for enantiomeric analysis of
amines based on coupling reactions with methanephosphonic acid dichlo
ride. (C) 1994 Wiley-Liss, Inc.