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Efficient enantiodiscrimination of chiral monophosphine oxides and boranes by phosphorus coupled 13C NMR spectroscopy in the presence of chiral ordering agents

✍ Scribed by Michaël Rivard; Frédéric Guillen; Jean-Claude Fiaud; Christie Aroulanda; Philippe Lesot

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
314 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

The synthesis of new chiral phospholanes via the corresponding oxides or boranes is reported and the analytical potential of 13 C-{ 1 H} NMR spectroscopy in weakly ordering polypeptide liquid crystalline phases in view to differentiate between enantiomers of these chiral phosphines precursors is explored. In particular results involving organic solutions of poly-g-benzyl-Lglutamate (PBLG) and poly-o-carbobenzyloxy-L-lysine (PCBLL) are described. This NMR approach allows determination of the enantiomeric composition, and provides therefore a new efficient alternative to classical methods usually used to analyze this class of compounds. A description of various spectral enantiodifferentiation patterns expected to be observed using 13 C-{ 1 H} NMR of enantiomers having a spin-1/2 heteroatomic nucleus, embedded in a chiral liquid crystal is presented.

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