Effects of compound structure and temperature on the resolution of enantiomers of cyclopentenones by liquid chromatography on derivatized cellulose chiral stationary phases

Abstract Analytical HPLC methods using derivatized cellulose chiral stationary phases were developed for the separation of the enantiomers of eight cyclopentenone derivatives. The mobile phase and the chiral stationary phase were varied to achieve the best resolution. It was shown that the chemical environment distant from the chiral center had large effects on the separation obtained. The effect of subambient and elevated temperature on the retention, separation and the resolution of the enantiomers was also investigated. Maximum resolution was obtained at elevated temperatures. Three of the compounds were scaled up to preparative loadings to determine the correlation between analytical resolution and preparative resolution. In addition, an example of the sample self-displacement effect observed during the preparative resolution of one of these compounds will be discussed.