DIMETHYLPHENYLCARBAMATES, DICHLOROPHENYLCARBAMATES AND CHLOROMETHYLPHENYLCARBAMATES OF AMYLOSE AS CHIRAL STATIONARY PHASES FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY

Twelve dimethyl-, dichloro- and chloromethylphenylcarbamate derivatives of amylose were prepared and their chiral recognition abilities were evaluated as chiral stationary phases for high-performance liquid chromatography. ortho-Substituted phenylcarbamate derivatives of amylose showed high chiral recognition abilities, although cellulose phenylcarbamate derivatives with ortho substituents on the phenyl moiety showed low chiral recognition. The superiority of 5-chloro-2-methylphenylcarbamate over the corresponding dimethyl- and dichlorophenylcarbamate derivatives of amylose was demonstrated. The roles of the NH residue of the carbamate moieties and methyl and chloro groups in chiral recognition were elucidated using IR and H-1 NMR spectroscopic data. The tris(5-chloro-2-methylphenylcarbamate) of amylose exhibited the highest chiral recognition ability among the amylose derivatives synthesized, and can be used for the separation of some chiral drug enantiomers.