Enantioseparation by HPLC using phenylcarbonate, benzoylformate, p-toluenesulfonylcarbamate, and benzoylcarbamates of cellulose and amylose as chiral stationary phases

Phenylcarbonate, benzoylformate, and p-toluenesulfonylcarbamate of cellulose and five new benzoylcarbamate derivatives of both cellulose and amylose were synthesized and their chiral recognition abilities were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Cellulose benzoylcarbamate has a higher chiral recognition ability compared to phenylcarbonate, p-toluenesulfonylcarbamate, and benzoylformate of cellulose. The benzoylcarbamate derivatives exhibited a characteristic chiral recognition for the racemates, which bear a hydrogen atom capable of hydrogen bonding to the carbonyl group of the benzoylcarbamates. The structures of the benzoylcarbamates were investigated by CD spectroscopy.