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Synthesis of β-keto carboxylic acids, esters and amides

Name Reactions


Claisen Condensation


Dieckmann Condensation


Recent Literature


Mild and Efficient Pentafluorophenylammonium Triflate (PFPAT)-Catalyzed C-Acylations of Enol Silyl Ethers or Ketene Silyl (Thio)Acetals with Acid Chlorides
A. Iida, J. Osada, R. Nagase, T. Misaki, Y. Tanabe, Org. Lett., 2007, 9, 1859-1862.


A Ti-crossed Claisen condensation between ketene silyl (thio)acetals and acid chlorides gave α-monoalkylated (thio)esters and thermodynamically unfavorable α,α-dialkylated β-keto (thio)esters in good yield. The protocol was extended to the direct condensation of ketene silyl acetals with carboxylic acids.
A. Iida, S. Nakazawa, T. Okabayashi, A. Horii, T. Misako, Y. Tanabe, Org. Lett., 2006, 8, 5215-5218.


A. Iida, S. Nakazawa, T. Okabayashi, A. Horii, T. Misako, Y. Tanabe, Org. Lett., 2006, 8, 5215-5218.


Thioesters undergo chemoselective soft enolization and acylation by N-acylbenzotriazoles on treatment with MgBr2ˇOEt2 and i-Pr2NEt to give β-keto thioesters without prior enolate formation. The reaction is conducted using untreated CH2Cl2 open to the air. The coupled products can be converted directly into β-keto esters, β-keto amides, and β-diketones under mild conditions.
G. Zhou, D. Lim, D. M. Coltart, Org. Lett., 2008, 10, 3809-3812.


Aromatic, aliphatic, and heterocyclic aldehydes are successfully condensed with ethyl diazoacetate in the presence of molybdenum(VI) dichloride dioxide as catalyst to obtain the corresponding β-keto esters in high yields at room temperature.
K. Jeyakumar, D. K. Chand, Synthesis, 2008, 1685-1687.


Aldehydes react readily with ethyl diazoacetate in the presence of 5 mol% of NbCl5 in dichloromethane to produce the corresponding β-keto esters in good yields with high selectivity. This method allows the preparation of β-keto esters from various aldehydes under mild reaction conditions.
J. S. Yadav, B. V. S. Reddy, B. Eeshwaraiah, P. N. Reddy, Tetrahedron, 2005, 61, 875-878.


The TiCl4-mediated reaction of esters with benzoyl chloride gave α-benzoylated esters in high yields.
D. F. Taber, R. B. Sheth, P. V. Joshi, J. Org. Chem., 2005, 70, 2851-2854.


A convenient two-step preparation of alkylidenepyrrolidines is reported.
M. C. Elliot, S. V. Wordingham, Synthesis, 2006, 1162-1170.