Origin of Enantioselectivity in Chiral Phosphoric-Acid-Catalyzed Azlactone Dynamic Kinetic Resolution
Pedro P. de Castro, Gabriel M. F. Batista, Giovanni W. Amarante, Hélio F. Dos Santos
Abstract
Theoretical calculations, associated with control experiments, were carried out to gain insights into the mechanism and origin of enantioselectivity in the phosphoric-acid-catalyzed dynamic kinetic resolution of azlactones. The results revealed a Münchnone intermediate as the key species involved in the isomerization of azlactone rings. The developed model was successfully employed in the comprehension and prediction of enantioselectivity under diverse of reaction conditions, including alcoholysis and aminolysis protocols.
Topics & Concepts
AminolysisKinetic resolutionPhosphoric acidIsomerizationCatalysisChemistryEnantioselective synthesisOptically activeCombinatorial chemistryComputational chemistryOrganic chemistrySynthesis and Reactions of Organic CompoundsAsymmetric Synthesis and CatalysisIonic liquids properties and applications