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Dieckmann Condensation

Lianyungang Klinechem Co.,Ltd | Updated: Dec 05, 2018

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
A. M. Armaly, S. Bar, C. S. Schindler, Org. Lett.201719, 3958-3961.

One-Pot Synthesis of Tetronic Acids from Esters
A. Mallinger, T. Le Gall, C. Mioskowski, Synlett2008, 386-388.

Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)
T. R. Hoye, V. Dvornikovs, E. Sizova, Org. Lett.20068, 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.200772, 7455-7458.

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