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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
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Published on: January 17, 2020

Enantioselective organocatalytic Diels-Alder reactions: a density functional theory and kinetic isotope effects study

Nasr Y M Omar1, Noorsaadah A Rahman, Sharifuddin M D Zain

  • 1Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.

Journal of Computational Chemistry
|April 2, 2011
PubMed

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In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
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The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.
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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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