Enantioselective troger's base synthetic receptors

Synthetic receptors selective for the enantiomers of Troger's base (1), a c ompound containing chiral nitrogen atoms, have been prepared by the molecul ar imprinting of 1 in methacrylic acid-ethylene glycol dimethacrylate copol ymers. Spectroscopic evaluation of the self-assembly phase, prior to polyme rization, demonstrated the formation of template-functional monomer adducts of K-diss 0.7 +/- 0.1 mM at 293 K in chloroform. The synthetic receptors d emonstrated enantioselectivity when used as HPLC chiral stationary phases; enantioseparation factors (alpha) of up to 4.8 +/- 0.2 are reported. Baseli ne resolution of racemic 1 was readily achieved. Furthermore, the influence of water on polymer-ligand selectivity was examined, which yielded insight s into the molecular basis for ligand selectivity in these synthetic recept ors. (C) 1999 Academic Press.