Enantiomeric Separations of N–H/N–Me Aziridines Utilizing GC and HPLC

Abstract

High-performance liquid chromatographic (HPLC) and gas chromatographic (GC) methods were developed for the separation of enantiomers of 12 novel aziridines. The HPLC separations were performed on cyclodextrin, cyclofructan, amylose, cellulose and macrocyclic glycopeptide-based chiral stationary phases, whereas the GC separations were performed only on cyclodextrin-based chiral stationary phases. The amylose-based HPLC chiral stationary phases showed good selectivity toward the aziridines, while having low retention factors. It was shown that the HPLC generally provided better separations for most of the compounds as compared to GC. Effective enantiomeric separations for ten aziridines were developed.