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Synthesis of 1,5-keto carboxylic acids, esters and amides


Recent Literature

An N-heterocyclic carbene (NHC) and photo-co-catalyzed alkylacylation of olefins in the presence of a diazo ester provides 1,5-ketoesters with great atom economy and N2 as the only byproduct. Particularly, this radical process employs a traditional carbene precursor as the radical source.
B. Zhang, J.-Q. Qi, Y. Liu, Z. Li, J. Wang, Org. Lett., 2022, 24, 279-283.

An efficient carbene-catalyzed formal [4 + 2] annulation of β-silyl enones with a HOBT ester followed by ring opening with nucleophiles provides γ-keto-β-silyl esters and amides, most with extremely high enantioselectivities. γ-Keto-β-silyl esters can be easily converted into enantioenriched β,σ-dihydroxyl esters.
Y. Zhang, X. Huang, J. Guo, C. Wei, M. Gong, Z. Fu, Org. Lett., 2020, 22, 9545-9550.

Enantioselective Mukaiyama-Michael Reaction of β,γ-Unsaturated α-Keto Esters with Silyl Ketene Acetals Catalyzed by a Chiral Magnesium Phosphate
H. He, X. Shen, X. Ding, J. C. Antilla, Org. Lett., 2023, 25, 782-787.