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., 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.