Dieckmann Condensation

The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic ß-keto esters, and is usually effected with sodium alkoxide in alcoholic solvent.

The yields are good if the product has an enolizable proton; otherwise, the reverse reaction (cleavage with ring scission) can compete. See the Claisen Condensation.

---

Mechanism of the Dieckmann Condensation

The mechanism is similar to the Claisen Condensation.

Recent Literature

Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones

One-Pot Synthesis of Tetronic Acids from Esters

Construction of Polycyclic β-Ketoesters Using a Homoconjugate Addition/Decarboxylative Dieckmann Annulation Strategy

Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)

An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters