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The intramolecular condensation of a diester, producing a cyclic β-keto ester, is called the Dieckmann condensation. The base abstracts an α-proton from one of the esters, yielding an enolate ion that attacks the other ester, forming a tetrahedral intermediate. Alkoxide ion is released, followed by the formation of a second base-mediated enolate ion. An acid work-up affords the final cyclic β-keto ester.
- Reagents: Metal Alkoxide, Alkoxide Base, Acid Work-up
- Reactant: Diester with α-Hydrogens
- Product: Cyclic β-Keto Ester
- Type of Reaction: Condensation
- Ion-Exchange Resins for Combinatorial Synthesis: 2,4-Pyrrolidinediones by Dieckmann Condensation. Angewandte Chemie International Edition in English. 1997, 36 (22), 2454-2455.
- Practical Synthesis of (Z)-Civetone Utilizing Ti-Dieckmann Condensation. Advanced Synthesis & Catalysis. 2002, 344 (5), 507-510.
- Clasien Condensation
- Metal Alkoxide
- Alkoxide Base
- Acid Work-up