Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of β-keto carboxylic acids, esters and amides
Name Reactions
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.
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.
A new carbamoyl Baker-Venkataraman rearrangement is described. The
starting acylketones for the rearrangement are efficiently prepared via a
Directed ortho
Metalation - Negishi cross coupling protocol from arylcarbamates. The
overall sequence provides a regiospecific anionic Friedel-Crafts complement
for the construction of ortho-acyl phenols and coumarins.
A. V. Kalinin, A. J. M. Da Silva, C. C. Lopes, R. S. C. Lopes, V. Snieckus,
Tetrahedron. Lett., 1998, 39, 4995-4998.
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.
