Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives

Bui, Tam T.T., Coles, Simon J., Davies, David B., Drake, Alex F., Eaton, Robert J., Hursthouse, Michael B., Kiliç, Adem, Shaw, Robert A. and Yeşilot, Serkan (2005) Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives. Chirality, 17 (8), 438-443. (doi:10.1002/chir.20187).

Abstract

The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled 31P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:1 ratio, consistent with formation of diastereoisomers. The meso and racemic forms of compound 2 were separated by column chromatography on silica gel and characterised by elemental analysis, mass spectrometry, 31P NMR spectroscopy, and X-ray crystallography. Using HPLC with a chiral stationary phase, the racemic form of compound 2 was further separated into enantiomers, which were characterised by circular dichroism (CD) spectroscopy. This is the first report of the separation of enantiomers in the field of cyclophosphazene chemistry and hence the first CD spectra of derivatives in which the cyclophosphazene ring is at the chiral centre.

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