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RESEARCH PRODUCT
Enantiodifferentiation of acyclic phosphonium salts in chiral liquid crystalline solutions
Sylvain JugéAbdelkrim MeddourJacques UzielJacques Courtieusubject
Alternative methodsChemistryLiquid crystallineOrganic ChemistryCarbon-13 NMRCatalysisStereocenterInorganic ChemistryNMR spectra databasechemistry.chemical_compoundCrystallographyLiquid crystalOrganic chemistryPhosphoniumPhysical and Theoretical ChemistryEnantiomerdescription
Abstract The enantiodifferentiation of acyclic phosphonium salts bearing a stereogenic centre, whether on the phosphorus atom or on one of its substituents, was investigated by 2 H–{ 1 H}, 13 C–{ 1 H} and 31 P–{ 1 H} NMR in chiral liquid crystals composed of a polypeptide dissolved in an organic solvent. For the first time, the enantiomers of P-chirogenic phosphorus compounds were discriminated in these anisotropic media, affording good to excellent separation of the signals, allowing the determination of their proportion. While 31 P–{ 1 H} NMR spectra showed no chiral separation, 2 H–{ 1 H} NMR was efficient in the enantiodifferentiation of an isotopically labelled compound. Better still, 31 C–{ 1 H} NMR in chiral liquid crystal appears as a powerful method for the enantiodifferentiation of this class of compounds, since separations of the signal up to 0.8 ppm were observed. In this commercially available anisotropic medium, 2 H and 13 C NMR offers a new promising alternative method for the enantiodifferentiation of chiral phosphonium salts.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-05-01 | Tetrahedron: Asymmetry |