Direct enantiomeric separation of β-aminoalcohols and β-hydroxy sulfides using polysaccharide derivatives as chiral stationary phases

Direct enantiomeric separation of racemic mixtures of 13 beta - amino alcohols and beta - hydroxy sulfides was achieved by HPLC using Chiralcel OD, Chiralcel OJ and Chiralpak AD as chiral stationary phases and hexane/2 - propanol mixture as eluent. These racemates were completely separated into enantiomers at least on one of these stationary phases. The chromatographic parameters of these racemates on AD, OD and OJ columns at various ratios of hexane/2 - propanol were examined. The results showed that the properties of substituents of the compounds obviously had effects on their resolution on columns. The hydrogen bonding and pi - pi interactions between the chiral stationary phase and the polar group of racemates may be responsible for the chiral recognition. This method had been applied to determination of the optical purity of the product from asymmetric ring opening of meso - epoxides.