Enantiomeric recognition of chiral invertomers through NMR chiral orientedphases: a study of cis-decalin

We describe a deuterium 1D and 2D NMR study of cis-decalin in various chira l and achiral polypeptide oriented solvent systems and the effect of the ac quisition temperature. Organic solutions of poly-gamma -benzyl-L-glutamate (PBLG) or poly-epsilon -carbobenzyloxy-L-lysine (PCBLL) in dichloromethane or chloroform allow the chiral invertomers of cis-decalin to be differentia ted at low temperature. At high temperature, it is possible to distinguish between deuterium nuclei of the molecule which become enantiotopic under ra pid kinetic averaging. The results obtained illustrate the capability of su ch polypeptide liquid-crystalline solvents to enantioselectively interact w ith unfunctionalised chiral cycloalkanes and highlight the analytical poten tial of NMR analysis in chiral liquid crystal based solvents in the investi gation of interconverting chiral conformers, (C) 2001 Published by Elsevier Science Ltd.