Efficient enantiodiscrimination of chiral monophosphine oxides and boranes by phosphorus coupled 13C NMR spectroscopy in the presence of chiral ordering agents - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron: Asymmetry Année : 2003

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

Résumé

The synthesis of new chiral phospholanes via the corresponding oxides or boranes is reported and the analytical potential of 13C-{1H} 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--benzyl-Lglutamate (PBLG) and poly--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 13C-{1H} NMR of enantiomers having a spin-1/2 heteroatomic nucleus, embedded in a chiral liquid crystal is presented.

Dates et versions

hal-02310631 , version 1 (10-10-2019)

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Michael Rivard, F. 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, 2003, 14 (9), pp.1141-1152. ⟨10.1016/S0957-4166(03)00202-7⟩. ⟨hal-02310631⟩
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