Optical Resolution of Alcohols as Carbamates by HPLC on Cellulose Tris(phenylcarbamate) Derivatives

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Abstract
The optical resolutions of various alcohols as phenylcarbamates were examined by HPLC on chiral stationary phases derived from sixteen cellulose tris(phenylcarbamate) derivatives. The optical resolving power of chiral stationary phases was greatly influenced by substituents on the phenyl groups of the cellulose derivatives. Also, cellulose tris(3,5-dimethylphenylcarbamate) could very efficiently resolve many racemic phenylcarbamates, including the carbamates of 2-butanol, 3-buten-2-ol, and 1-phenylethanol. Racemic phenylcarbamates having electron-donating substituents on the phenyl group were better resolved than those having electron-withdrawing substituents. The benzoates of most alcohlos were not resolved as efficiently as the carbamates.