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
Mechanism
Top Citations
Original Paper
Related Reactions
- Alder-ene Reaction
- 1,3-dipolar Cycloaddition
- Synthesis of cyclohexenes
Related Compounds
- Conjugated diene
- Dienophile
