Efficient enantiodiscrimination of chiral monophosphine oxides and boranes by phosphorus coupled 13C NMR spectroscopy in the presence of chiral ordering agents - Université Paris-Est-Créteil-Val-de-Marne Access content directly
Journal Articles Tetrahedron: Asymmetry Year : 2003

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 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.

Dates and versions

hal-04013355 , version 1 (03-03-2023)

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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, 2003, 14, pp.1141 - 1152. ⟨10.1016/s0957-4166(03)00202-7⟩. ⟨hal-04013355⟩
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