Z. Glowacki et al., DIRECT P-31 NMR DETERMINATION OF THE ENANTIOMERIC COMPOSITION OF 1-HYDROXYALKYLPHOSPHONATES USING 1-(1-NAPHTHYL)ETHYLAMINE AS A CHIRAL AGENT, Phosphorus, sulfur and silicon and the related elements, 82(1-4), 1993, pp. 39-47
Optically active 1-(1-naphthyl)ethylamine and 1-hydroxyalkylphosphonic
acids form in nonpolar solvents diastereoisomeric salts distinguished
in P-31 NMR spectroscopy. The magnetic nonequivalence of phosphonate
groups is large enough (esp. for benzyl monoesters salts DELTAdeltaP-3
1 is up to 0.36 ppm) to determine ee values. The dependence of diaster
eoisomeric salts magnetic nonequivalence on concentration and enantiop
urity of amine component is studied.