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

Abstract

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, H-1 and P-31 NMR spectroscopies. The enantiomers of newly synthesised compounds have been analysised by the changes in the P-31 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. (c) 2009 Elsevier B.V. All rights reserved.