Enantiomeric recognition of chiral invertomers through NMR in chiral oriented phases: a study of cis-decalin

Abstract : We describe a deuterium 1D and 2D NMR study of cis-decalin in various chiral and achiral polypeptide oriented solvent systems and the effect of the acquisition temperature. Organic solutions of poly-γ-benzyl-l-glutamate (PBLG) or poly-ε-carbobenzyloxy-l-lysine (PCBLL) in dichloromethane or chloroform allow the chiral invertomers of cis-decalin to be differentiated at low temperature. At high temperature, it is possible to distinguish between deuterium nuclei of the molecule which become enantiotopic under rapid kinetic averaging. The results obtained illustrate the capability of such polypeptide liquid-crystalline solvents to enantioselectively interact with unfunctionalised chiral cycloalkanes and highlight the analytical potential of NMR analysis in chiral liquid crystal based solvents in the investigation of interconverting chiral conformers.
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Submitted on : Wednesday, October 9, 2019 - 8:35:13 AM
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Muriel Sarfati, Christie Aroulanda, Jacques Courtieu, Philippe Lesot. Enantiomeric recognition of chiral invertomers through NMR in chiral oriented phases: a study of cis-decalin. Tetrahedron: Asymmetry, Elsevier, 2001, 12 (5), pp.737-744. ⟨10.1016/S0957-4166(01)00103-3⟩. ⟨hal-02309129⟩

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