Chiral ionic liquids based on nicotine for the chiral recognition of carboxylic acids

The synthesis of enantiopure ionic liquids based on (-)-nicotine is discussed. The desired compounds were prepared in good yields from (-)-nicotine via quaternization of the pyridine ring of (-)-nicotine with MeI and EtBr. After anion metathesis the ionic liquids were investigated as chiral solvating agents and showed a splitting of the signals of Mosher's acid and mandelic acid in the H-1 and F-19 NMR spectra. In addition to aprotic solvents it was also possible to use methanol in the experiments. (C) 2013 Elsevier Ltd. All rights reserved.