Density Functional Theory Calculations: A Useful Tool to Investigate Mechanisms of 1,3-Dipolar Cycloaddition Reactions

Int J Mol Sci. 2024 Jan 20;25(2):1298. doi: 10.3390/ijms25021298.

Abstract

The present review contains a representative sampling of mechanistic studies, which have appeared in the literature in the last 5 years, on 1,3-dipolar cycloaddition reactions, using DFT calculations. Attention is focused on the mechanistic insights into 1,3-dipoles of propargyl/allenyl type and allyl type such as aza-ylides, nitrile oxides and azomethyne ylides and nitrones, respectively. The important role played by various metal-chiral-ligand complexes and the use of chiral eductors in promoting the site-, regio-, diastereo- and enatioselectivity of the reaction are also outlined.

Keywords: DFT calculations; aza-ylides; azomethine ylides; dipolar cycloadditions; nitrile oxides; nitrones.

Publication types

  • Review

MeSH terms

  • Cycloaddition Reaction
  • Density Functional Theory
  • Nitriles*

Substances

  • Nitriles

Grants and funding

The authors thank the Universities of Catania and Milano-Bicocca for partial financial support. M.A.C., thanks MIUR (NextGenerationEu, Bando 2022 PNRR Prot. P20224MN78).