How the mechanism of a [3 + 2] cycloaddition reaction involving a stabilized N-lithiated azomethine ylide toward a π-deficient alkene is changed to stepwise by solvent polarity? What is the origin of its regio- and endo stereospecificity? A DFT study using NBO, QTAIM, and NCI analyses

The regio- and endo stereospecific 32CA reaction of the stabilized N-lithiated azomethine ylide 2 toward the π-deficient alkene 3in THF occurs to afford cycloadduct 6via a stepwise mechanism, passing through the zwitterionic intermediate 4.