Preparation of cellulose derivative bearing bulky 4‐(2‐benzothienyl)phenylcarbamate substituents as chiral stationary phase for enantioseparation

Abstract

A novel cellulose derivative bearing bulky 4-(2-benzothienyl)phenylcarbamate substituents (Cel-1) was readily synthesized by carbamoylation followed by Suzuki-Miyaura coupling reaction. The corresponding coated-type chiral stationary phase (CSP) was prepared on basis of the derivative, and its chiral recognition ability was then evaluated by high-performance liquid chromatography (HPLC). The chiral recognition ability of the cellulose derivative was greatly influenced by introduction of the bulky benzothienyl pendants on the aromatic moieties of phenylcarbamates, compared with its analog with smaller groups. Many racemates, including the metal tris(acetylacetonate) complexes, chiral drug, and the analyte with axial chirality, were sufficiently separated