Intramolecular Hydrogen Bond Activation of Aza-Methylene Imines in Hydrogen Bond Bifunctional Catalysis – A Density Functional Theory Study

Abstract

In this work, we present a density functional theory study of the dipolar cycloaddition of azamethylene imines to nitroalkenes, showing the importance of the intramolecular activation of the hydroxyl group and the role of the intermolecular hydrogen bond with Takemoto's catalyst. The importance of non-covalent interactions is evaluated by means of simulations using non-covalent interactions, and natural bonding orbital analysis. The combination of these studies allows us to understand the role played by the intra- and intermolecular interactions in the reactivity and enantioselectivity of the process.