迪克曼缩合_Dieckmann缩合_Dieckmann Condensation
碱催化的二酯的分子内缩合。 Dieckmann缩合法可很好地生产5-或6-元环状β-酮酸酯,通常在醇溶剂中用醇钠进行。
如果产品具有可烯醇化的质子,则产率良好; 否则,逆反应(与环断裂的解理)可以竞争。 参见Claisen Condensation。
Dieckmann缩合机理
该机制类似于Claisen Condensation。
近期文献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.
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.