Enantioseparation on fluoro-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatography

Abstract

Six phenylcarbamate derivatives of cellulose and amylose having both an electron-withdrawing fluoro group and an electron-donating methyl group on the phenyl moieties were synthesized, and their chiral recognition abilities were evaluated as chiral stationary phases for high-performance liquid chromatography. The resolving abilities were compared with those of chloro-methylphenylcarbamate derivatives of cellulose and amylose. The chiral recognition abilities of fluoro-methylphenylcarbamates of cellulose and amylose were dependent on the position of the substituents. The cellulose derivatives with fluoro and methyl groups at the meta and para positions showed higher resolving power than the ortho- and meta-disubstituted derivative as observed for the chloro-methylphenylcarbamate derivatives of cellulose. On the other hand, the ortho-substituted derivative of amylose, tris(5-fluoro-2-methylphenylcarbamate), showed high chiral recognition as well as the meta- and para-disubstituted derivatives. The different chiral recognition was discussed on the basis of IR and CD spectroscopic data. © 1995, The Society of Polymer Science, Japan. All rights reserved.