Direct enantiomeric separation of acetylenylaziridines using polysaccharide derivatives as chiral stationary phases

Direct enantiomeric separation? of racemic mixtures of 15 acetylenylaziridines was achieved by HPLC using Chiralpak AD and Chiralcel OD as chiral stationary phases and with hexane-2-propanol mixture as an eluent. These acetylenylaziridines were completely separated into enantiomers at least on one of the stationary phases. The chromatographic parameters of these racemates on AD and OD columns using various hexane-2-propanol concentrations were examined. The results showed that the different configuration and higher order stucture of the glucose residues of the stationary phases and interactions between dimethylphenylcarbamate group of chiral stationary phase and the polar groups of aziridines may be responsible for the chiral recognition. This method has been used to identify the optical purity of the products from asymmetric aziridination.