Enantiomeric separation of epoxides by gas chromatography using derivatized Beta-cyclodextrin as stationary phase

Abstract

Eanatiomeric separations of aromatic epoxides were studied by means of capillary gas chromatography using heptakis(2,3,di-O-methyl-6-O-tert-butyldi methylisilyl)cyclomaltoheptaose (or BSiMe) and heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsiloyl)cyclomaltoheptaose (or BSiAc) as chiral stationary phases. The effects of substitution types and position of styrene oxide derivatives on retention and enantioselectivity have been investigated. Thermodynamic data on the interaction of enantiomers with chiral stationary phases were collected in detail in order to clarify the strength of analyte-stationary phase interaction and enantioselectivity towards the selected groups of epoxides. All eposides with different substitution type and position were successfully separated with either BSiMe or BSiAc, or otherwise both of them. On both columns, the number, type, and position of analyte substitution have a strong influence on enantioselectivity. The type of substituent on cyclodextrin molecule (BSiMe vs.BSiAc) also affect enatioselectivity of epoxides greatly. Both columns can be used to compliment one another as their resolving abilities are quite opposite.