The mechanism investigation of the imidazolidinone catalyzed five‐membered ring synthesis reaction

Abstract

The intramolecular asymmetric Michael addition reaction catalyzed by imidazolidinone is investigated using the density functional theory calculations. The details of the reaction mechanism, potential energy surfaces, and the influence of the acid additive are investigated. The reaction process includes two stages. The first stage is Michael addition, in which the enamine complex is created and then the Michael addition is carried out. The second stage is a product separation stage which includes an enol-keto tautomerization and a two-step hydrolysis. The enantioselectivity is controlled by the Michael addition step which involves a new carbon-carbon bond formation. The calculation results provide a general model which may explain the mechanism and enantioselectivity of the title reaction.