Orbital - Vol. 11 No. 1 - January-March 2019
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DFT Studies on the Stereoselective Three-Component Ugi Reaction

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  • Elaheh Sadat Sharifzadeh,
  • Nader Zabarjad Shiraz
Elaheh Sadat Sharifzadeh
Department of Chemistry, Islamic Azad University, Central Tehran Branch, 146786831, Tehran, IRAN
Nader Zabarjad Shiraz
Department of Chemistry, Islamic Azad University, Central Tehran Branch, Tehran, IRAN
Published March 30, 2019
Keywords
  • DFT calculation,
  • multicomponent reaction,
  • stereoselectivity,
  • three-component Ugi reaction
How to Cite
(1)
Sharifzadeh, E. S.; Shiraz, N. Z. DFT Studies on the Stereoselective Three-Component Ugi Reaction. Orbital: Electron. J. Chem. 2019, 11, 18-24.

Copyright (c) 2019 Orbital: The Electronic Journal of Chemistry

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Abstract

studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, including atom inversion, bond rotation, acid-base, nucleophile-electrophile competitions. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, the enthalpy of the reaction was -45.9 and -41.2 kcal/mol for the dominant product in gas phase and in methanol. The stereoselectivity of the reaction was under the kinetic control of nucleophilic attack of isocyanide to less hindered si-face (Ea= 4.1       compared to 7.4 kcal/mol for re-face) of more stable chiral (E)-iminium in methanol.

DOI: http://dx.doi.org/10.17807/orbital.v11i1.1214

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