Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives
| Autor: | David B. Davies, Robert A. Shaw, Robert J. Eaton, Alex F. Drake, Serkan Yeşilot, Michael B. Hursthouse, Adem Kılıç, Tam T.T. Bui, Simon J. Coles |
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| Rok vydání: | 2005 |
| Předmět: |
Circular dichroism
Magnetic Resonance Spectroscopy Stereochemistry Phosphoranes Crystallography X-Ray Piperazines Catalysis Analytical Chemistry Stereocenter chemistry.chemical_compound Column chromatography Drug Discovery Chiral derivatizing agent Piperazine Chromatography High Pressure Liquid Spectroscopy Pharmacology Molecular Structure Circular Dichroism Organic Chemistry Diastereomer Phosphorus Isotopes Stereoisomerism Chiral column chromatography Crystallography chemistry Enantiomer |
| Zdroj: | Chirality. 17:438-443 |
| ISSN: | 1520-636X 0899-0042 |
| DOI: | 10.1002/chir.20187 |
| Popis: | 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 (31)P 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, (31)P 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. |
| Databáze: | OpenAIRE |
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