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
Mechanism
Top Citations
Original Paper
Related Reactions
- Clasien Condensation
Related Compounds
- Metal Alkoxide
- Alkoxide Base
- Acid Work-up
