Abstract
AbstractDFT calculations involving the B3LYP functional and 6‐31G(d) basis set have been performed to rationalize the reactivity, regioselectivity, enantioselectivity and diasteriofacial selectivity in the context of 1,3‐dipolar cycloaddition (13DC) reactions of a few acyclic and two cyclic azomethine ylides (AY) leading to enantiomeric/ diasteriomeric excess of the products. In particular, N‐substituted and C‐substituted AYs have been considered for reactions with the substituted ethylenes, maleimide, maleic anhydride and methyl acrylate. From an analysis of the results of calculation for the selected reactions, the regio‐ and exo/endo‐stereoselectivity have been explained. Reactions were followed through transition state (TS) structure optimization, calculation of IRC and activation energies. A rationalization of the trends in regioselectivity and enantioselectivity was attempted with the help of HOMO–LUMO energies, electrophilicity differences (Δω) and an analysis of Pauling's bond order (PBO) in the TS. Copyright © 2009 John Wiley & Sons, Ltd.
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