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Alkali Carbonates Improve β,β-Diaryl Serine-Catalyzed Enantioselective α-Fluorination of β-Dicarbonyl Compounds
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2023-05-25 , DOI: 10.1021/acs.joc.3c00730
Katsuki Endo 1 , Daiki Tomon 1 , Satoru Arimitsu 1
Affiliation  

Herein, we report the highly enantioselective α-fluorination of both cyclic and acyclic β-dicarbonyl compounds, including β-diketones, β-ketoesters, and β-ketoamides. The reactions with β,β-diaryl serines as primary amine organocatalysts were enhanced by adding alkali carbonates, such as Na2CO3 or Li2CO3, and enabled the reaction to be conducted with only 1.1 equiv of Selectfluor. The optimal conditions afforded the α-fluorinated β-dicarbonyl compounds in 50–99% yield with excellent enantioselectivity (up to 98% ee).

中文翻译:

碱金属碳酸盐改善 β-二羰基化合物的 β,β-二芳基丝氨酸催化的对映选择性 α-氟化反应

在此,我们报道了环状和无环β-二羰基化合物(包括β-二酮、β-酮酯和β-酮酰胺)的高度对映选择性α-氟化。通过添加碱金属碳酸盐,例如Na 2 CO 3或Li 2 CO 3 ,可以增强以β,β-二芳基丝氨酸作为伯胺有机催化剂的反应,并且使得反应能够仅用1.1当量的Selectflu进行。最佳条件提供了 α-氟化 β-二羰基化合物,产率为 50-99%,具有优异的对映选择性(高达 98% ee)。
更新日期:2023-05-25
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