Organic Chemistry Portal
Reactions >> Name Reactions

Further Information

Related Reactions
Claisen Condensation

Dieckmann Condensation

The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic -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
A. M. Armaly, S. Bar, C. S. Schindler, Org. Lett., 2017, 19, 3958-3961.

One-Pot Synthesis of Tetronic Acids from Esters
A. Mallinger, T. Le Gall, C. Mioskowski, Synlett, 2008, 386-388.

Construction of Polycyclic β-Ketoesters Using a Homoconjugate Addition/Decarboxylative Dieckmann Annulation Strategy
Z. Chen, A. Y. Hong, X. Linhu, J. Org. Chem., 2018, 83, 6225-6234.

Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)
T. R. Hoye, V. Dvornikovs, E. Sizova, Org. Lett., 2006, 8, 5089-5091.

An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters
M. R. DeGraffenreid, S. Bennett, S. Caille, F. Gonzalez-Lopez de Turiso, R. W. Hungate, L. D. Julian, J. A. Kaizerman, D. L. McMinn, D. Sun, X. Yan, J. P. Powers, J. Org. Chem., 2007, 72, 7455-7458.