Journal of Fluorine Chemistry 2018-03-29

Straightforward synthesis of fluorinated amino acids by Michael addition of ethyl bromodifluoroacetate to α,β-unsaturated α-amino acid derivatives

Ivan S. Kondratov, Maxym Ya. Bugera, Nataliya A. Tolmachova, Constantin G. Daniliuc, Günter Haufe

Index: 10.1016/j.jfluchem.2018.03.014

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Abstract

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.