HYDROLYSE ENANTIOSELECTIVE D'ESTERS D'AMINOACIDE CATALYSEE PAR L'IMIDAZOLE DANS DES MICELLES INVERSES CHIRALES.1300

Article abstract of DOI:10.1016/S0040-4020(01)89932-4

This paper reports the study of the imidazole catalyzed hydrolysis of enantiomeric pairs of three aminoacid esters in reversed micelles prepared from water, heptane and a combination of both racemic or chiral surfactants and of both racemic or chiral (S)2-octanol as cosurfactants.The enantioselectivity observed is important in the combination of chiral surfactant with racemic cosurfactant, and small in the combination of racemic surfactant with chiral cosurfactant, when ω = 20 (ω = / ).This enantioselectivity is also affected by the nature of the cosurfactant, the size of micelles and the nature of the substrate.The results prove that the reaction occurs effectively in a chiral microenvironment, the micelle membrane, and indicate that the cosurfactant is actually present in this membrane.