F. Grosjean et al., MOLECULAR MODELING OF REGIOSELECTIVITY OF GLYCIDIC ACID OPENING REACTIONS BY ALIPHATIC-AMINES, Tetrahedron, 50(31), 1994, pp. 9325-9334
A model for glycidic acids opening reaction by ammonia and amines has
been suggested from semi-empiric orbital calculations. It provides a w
ay for evaluating the different interactions between the incoming nucl
eophile and the oxirane substituents. Steric and coulombic interaction
s of the carboxylate in staggered conformation (cis substitution) has
a major influence to rationalize experimental regioselectivity.