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

Related Compounds