Proceeding through a concerted, aromatic transition state, the Diels-Alder [4π+2π] cycloaddition uses heat to form a cyclohexene derivative from an electron rich (s-cis) diene and an electron poor dienophile (referred to as the normal electron-demand Diels-Alder reaction). Benefits include the conservation of the starting dienophile’s stereochemistry and the high regioselectivity and stereoselectivity seen with unsymmetrical dienes and dienophiles.

  • Reactant: Electron Rich s-cis Diene, Electron Poor Dienophile (Alkene, Substituted Alkyne, Benzyne, Allene)
  • Product: Cyclohexene Derivative
  • Type of Reaction: [4π+2π] Cycloaddition


Top Citations

Original Paper

Related Reactions

  • Alder-ene Reaction
  • 1,3-dipolar Cycloaddition
  • Synthesis of cyclohexenes

Related Compounds

  • Conjugated diene
  • Dienophile
By shuhan yang


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