A. Dobashi, S. Hara
1983
Citations
0
Influential Citations
21
Citations
Journal
Journal of Chromatography A
Abstract
Abstract The addition of chiral N-acetyl- L -valine-tert.-butylamide to the mobile phase using a silica gel column resulted in the optical resolution of D - and L -amino acid derivatives of N-acetyl-O-tert.-butyl esters. This is the first instance of enantioselectivity generated by diastereomeric chelate-like solvates based on intermolecular hydrogen bonds between the chiral additive and amino acid enantiomers. The degree of enantioselection was found to depend markedly on the composition of the chloroform—n-hexane mobile phase containing the chiral additive. The chromatographic process responsible for the recognition of the enantiomers is discussed on the basis of the equilibrium relationship in the column, involving the chiral additive and amino acid derivatives to be resolved.