Categories: C-C Bond Formation > Oxygen-containing molecules > Carboxyl derivatives >
Synthesis of 1,4-keto carboxylic acids, esters and amides
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Recent Literature
In a Co-catalyzed reaction for the construction of 1,4-dicarbonyls, a cascade
organocobalt addition/trapping/Kornblum-DeLaMare rearrangement were involved.
The reaction offers easy availability of starting materials, wide substrate
scope, high functionality tolerance, and operational simplicity.
F. Zhang, P. Du, J. Chen, H. Wang, Q. Luo, X. Wan, Org. Lett., 2014,
16, 1932-1935.
A visible-light-induced deaminative alkylation of Katritzky salts with silyl
enol ethers proceeds efficiently through electron donor-acceptor complex
formation. A series of functionalized γ-ketoesters was successfully obtained
with good functional group tolerance under mild, metal-free, and straightforward
conditions.
J.-X. Wang, W. Ge, W.-L. Xing, M.-C. Fu, J. Org. Chem., 2021, 86,
18224-18231.
A mild and highly efficient photocatalytic oxidative radical addition
reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds utilizes a
desulfurization process to generate electrophilic radicals, which add to
α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl
compounds.
Y. Dong, R. Li, J. Zhou, Z. Sun, Org. Lett., 2021, 23,
6387-6390.
A general and efficient copper-catalyzed alkylation of silyl enol ethers with
functionalized alkyl bromides provides sterically hindered γ-ketoesters under
mild conditions in good yields. The strategy can be used for the synthesis of
biologically active histamine H3 receptor antagonists.
D. Li, J. Org. Chem., 2021, 86,
515-524.
Visible light irradiation promotes the synthesis of α-substituted γ-ketoester
derivatives through carbene insertion and the decarbonylation of enaminones and
diazoesters. These reactions use readily available starting materials and
transition-metal-free, eco-friendly procedures that are amenable to gram-scale
synthesis and wide functional group tolerance.
W. Li, Y. Yang, Z. Tang, X. Yu, J. Lin, Y. Jin, J. Org. Chem., 2022, 87,
13352-13362.
Visible light irradiation promotes the synthesis of α-substituted γ-ketoester
derivatives through carbene insertion and the decarbonylation of enaminones and
diazoesters. These reactions use readily available starting materials and
transition-metal-free, eco-friendly procedures that are amenable to gram-scale
synthesis and wide functional group tolerance.
W. Li, Y. Yang, Z. Tang, X. Yu, J. Lin, Y. Jin, J. Org. Chem., 2022, 87,
13352-13362.