Abstract
Enantiomer content of secondary alkanol (1) by normal phase HPLC was determined using (R) - (-) -and (S) - (+) -1- (1-naphthyl) ethyl isocyanates [(R) -NEI and (S) -NEI] as chiral resolving reagents. Alcohol (1) reacted with NEI to give the corresponding diastereomeric carbamate (2), which was separated on achiral stationary phases. In the case of (R) -NEI, (S) isomer of (1) eluted more quickly than its (R) isomer, and vice versa for (S) -NEI. Separation factors decreased as the position of the hydroxyl group of (1) was close to the center of the carbon chain of (1). By the present method, determination was also made of the optical purity of 2-alkyl butyrate formed by lipase-catalyzed transesterification between tributyrin (tributyrylglycerol) and 2-alkanol in an organic solvent. The optical purity of the butyrate as determined by the above method showed good agreement with that found by optical rotation.
