DIRECT RESOLUTION OF ENANTIOMERS OF BASIC IMIDAZOL-2-YL-SUBSTITUTED ALCOHOLS BY GAS-CHROMATOGRAPHY ON CHIRASIL-VAL

The direct resolution of enantiomers of a series of imidazol-2-yl-subs tituted alcohols has been achieved by gas chromatography on a well-dea ctivated fused-silica capillary column, coated with L-Chirasil-Val as the chiral stationary phase. The separation of these basic compounds i s accomplished without exaggerated peak tailing. Compared to simpler a lcohols the resolution factors (alpha) observed are extraordinarily la rge. While the imidazolyl substituent may contribute to the mechanism of the chiral discrimination, the crucial interaction is assumed to be through the hydroxy group, based on the observation that the resoluti on factors for the corresponding 0-acetyl derivatives are markedly red uced. (C) 1993 Wiley-Liss, Inc.