Alkali Carbonates Improve β,β-Diaryl Serine-Catalyzed Enantioselective α-Fluorination of β-Dicarbonyl Compounds

Katsuki Endo, Daiki Tomon and Satoru Arimitsu*

*Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nakagami, Nishihara 903-0213, Okinawa, Japan, Email: arimitsusci.u-ryukyu.ac.jp

K. Endo, D. Tomon, S. Arimitsu, J. Org. Chem., 2023, 88, 9037-9045.

DOI: 10.1021/acs.joc.3c00730

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Abstract

Enantioselective α-fluorination of both cyclic and acyclic β-dicarbonyl compounds with β,β-diaryl serines as primary amine organocatalysts was conducted with only 1.1 equiv of Selectfluor by adding alkali carbonates, such as Na₂CO₃ or Li₂CO₃. The reaction afforded α-fluorinated β-dicarbonyl compounds in good yield with excellent enantioselectivity.

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proposed transition state

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Enantioselective Fluorination of α-Substituted β-Diketones Using β,β-Diaryl Serines

S. Poorsadeghi, K. Endo, S. Arimitsu, Org. Lett., 2022, 24, 420-424.

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Key Words

α-fluoroketones, Selectfluor, organocatalysis

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ID: J42-Y2023