Synthesis and enantiomeric analysis of cyclotriphosphazene derivatives with one centre of chirality

A series of chiral cyclotriphosphazene compounds 2–9 in which the spiro 3-amino-1-propanoxy moiety provides the one centre of chirality have been synthesised and characterised by elemental analysis, MS, 1H and 31P NMR spectroscopies. The enantiomers of newly synthesised compounds have been analysed by the changes in the 31P NMR spectra on addition of a Chiral Solvating Agent (CSA), (S)-(+)-2,2,2-trifluoro-1-(9′-anthryl)ethanol. HPLC methods have been developed for the enantiomeric separations of chiral cyclotriphosphazenes containing one centre of chirality. It is found that chiral HPLC gave a good resolution of enantiomers of the racemic compounds 2–9 with resolution factors between 2.49 and 7.50 making them good candidates for enantiomeric separations and determination of absolute configuration.