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Straightforward synthesis of fluorinated amino acids by Michael addition of ethyl bromodifluoroacetate to α,β-unsaturated α-amino acid derivatives
Journal of Fluorine Chemistry ( IF 1.9 ) Pub Date : 2018-03-29 , DOI: 10.1016/j.jfluchem.2018.03.014
Ivan S. Kondratov , Maxym Ya. Bugera , Nataliya A. Tolmachova , Constantin G. Daniliuc , Günter Haufe

Copper-mediated Michael addition of ethyl bromodifluoroacetate to N-protected α,β-unsaturated α-amino acid esters was applied for straightforward synthesis of γ,γ-difluorinated analogues of glutamic acid (compound 1) and glutamine (compound 10). Moreover, a proline-based, sterically constrained analog of γ,γ-difluoroglutamic acid (compound 24) was prepared.



中文翻译:

通过将溴代二氟乙酸乙酯加成到α,β-不饱和α-氨基酸衍生物上来直接合成氟化氨基酸

铜介导的溴代二氟乙酸乙酯向N保护的α,β-不饱和α-氨基酸酯的迈克尔加成反应用于直接合成谷氨酸(化合物1)和谷氨酰胺(化合物10)的γ,γ-二氟类似物。此外,制备了基于脯氨酸的,空间受限的γ,γ-二氟谷氨酸类似物(化合物24)。

更新日期:2018-03-29
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