DFT study on the intramolecular nitrone-alkene cycloaddition reaction of the N-3-alkenylnitrone

► Using DFT to study the intramolecular nitrone-alkene cycloaddition (INAC) of N-3-alkenylnitrone. ► The substituent on the olefinic bond is sensitive to the regioselectivity of the INAC reaction. ► Both the thermodynamic and intrinsic contributions determine the Z-selectivity. ► Aromatic ring in the N-3-alkenylnitrone backbone enhances Z-selectivity and rate of INAC reaction.