The Use of Cyclodextrin-Based LC Stationary Phases for the Separation of Chiral Dihydrobenzofuran Derivatives

The enantiomeric separation of 12 chiral dihydrobenzofurans is reported on derivatized β-cyclodextrin stationary phases using high performance liquid chromatography. The hydroxypropyl β-cyclodextrin chiral stationary phase (CSP) with acetonitrile/water mobile phases was the most effective combination as it baseline separated 9 of the 12 compounds. The acetyl β-cyclodextrin and 2,3-dimethyl β-cyclodextrin CSPs were also effective in the reverse phase mode. The native β-cyclodextrin was far less effective than the non-aromatic derivatized CSPs. The aromatic functionalized CSPs showed no selectivity in the normal phase mode. Structural characteristics, such as substituent polarity and ring location, were important in the observed enantioselectivity.