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In three distinct steps, the Robinson annulation converts a ketone and an α,β-unsaturated ketone into a substituted cyclohexenone compound. First, the base creates an enolate ion intermediate, which reacts with the α,β-unsaturated ketone in a conjugate 1,4 addition (Michael reaction) to form a 1,5 diketone. An intramolecular aldol reaction occurs next, affording a cyclic β-hydroxy ketone. A final base-catalyzed dehydration affords the cyclohexenone product.
- Reagents: Base, Ethanol
- Reactant: Ketone, α,β-Unsaturated Ketone
- Product: Substituted Cyclohexenone
- Type of Reaction: Carbonyl Condensation Reaction (Michael and Intramolecular Aldol)
- Bond Formation: C-C (α-carbon of the ketone and the β-carbon of the unsaturated ketone) and C=C
- This reaction can also be acid-catalyzed.
- Although a one-pot process is possible, yields tend to be higher when the Michael adduct is isolated and then subjected to the aldol reaction.
- The Michael reaction works best when a stable enolate ion adds to an unhindered α,β-unsaturated ketone.
- A Proline-Catalyzed Asymmetric Robinson Annulation Reaction. Tetrahedron Letters 2000, 41 (36), 6951–6954.
- Base-Promoted Reactions in Ionic Liquid Solvents. The Knoevenagel and Robinson Annulation Reactions. Tetrahedron Letters 2001, 42 (35), 6053–6055.
- Michael Addition
- Aldol Condensation
- Aldol Addition
- Ethanol (CAS 64-17-5)