Etude par la Modelisation Moleculaire de la Regioselectivite de l'Ouverture des Acides Glycidiques par les Amines Aliphatiques

Article abstract of DOI:10.1016/S0040-4020(01)85509-5

A model for glycidic acids opening reaction by ammonia and amines has been suggested from semi-empiric orbital calculations.It provides a way for evaluating the different interactions between the incoming nucleophile and the oxirane substituents.Steric and coulombic interactions of the carboxylate in staggered conformation (cis substitution) has a major influence to rationalize experimental regioselectivity.