N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations

Palladium-catalyzed N-arylations of amino acid tert-butyl esters using 4-bromo-N,N-dimethylaniline as a coupling partner are reported. The resulting N-aryl amino acid esters are suitable building blocks for the synthesis of electron-rich N-aryl peptides, which undergo oxidative couplings to aminooxy...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-02, Vol.85 (3), p.1748-1755
Main Authors: Young, Hailey A, Guthrie, Quibria A. E, Proulx, Caroline
Format: Article
Language:English
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Summary:Palladium-catalyzed N-arylations of amino acid tert-butyl esters using 4-bromo-N,N-dimethylaniline as a coupling partner are reported. The resulting N-aryl amino acid esters are suitable building blocks for the synthesis of electron-rich N-aryl peptides, which undergo oxidative couplings to aminooxy groups to afford ketoxime peptides under mild conditions. N-aryl amino acid tert-butyl esters possessing unnatural side chains were also accessed via glycine Schiff base alkylation, further increasing the scope of Cα-substitution in ketoxime peptides.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02810