Design and synthesis of a chiral stationary phase containing a benz[ de]isoquinolinone skeleton : I. First chromatographic results

Abstract

A chiral stationary phase (CSP) derived from 3-(4′-glycidyloxyphenyl)-2,3-dihydro-1 H-benz[ de]isoquinolin-1-one was designed and synthesized according to the reciprocality concept. A coplanar arrangement of possible attractive sites of interaction is due to the rigid conformation of the chiral selector. It was demonstrated that this CSP exhibits a good chiral discrimination ability towards families of racemates such as 3,5-dinitrobenzoyl derivatives of α-amino esters and α-amino-amides. Significant enhancements of selectivity were observed when chloroform was used instead of ethanol as a polar modifier in hexane, emphasizing the major contribution of the nature of the mobile phase to the chiral recognition process.