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

Abstract : The synthesis of new chiral phospholanes via the corresponding oxides or boranes is reported and the analytical potential of C-13-{H-1} 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-gamma-benzyl-L-glutamate (PBLG) and poly-epsilon-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 C-13-{H-1} NMR of enantiomers having a spin-1/2 heteroatomic nucleus, embedded in a chiral liquid crystal is presented.
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Submitted on : Wednesday, April 29, 2015 - 2:44:38 PM
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Michaël Rivard, Frédéric Guillen, Jean-Claude Fiaud, Christie Aroulanda, Philippe Lesot. Efficient enantiodiscrimination of chiral monophosphine oxides and boranes by phosphorus coupled 13C NMR spectroscopy in the presence of chiral ordering agents. Tetrahedron: Asymmetry, Elsevier, 2003, 14 (9), pp.1141. ⟨10.1016/S0957-4166(03)00202-7⟩. ⟨hal-01146992⟩

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