N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations.
J Org Chem
; 85(3): 1748-1755, 2020 02 07.
Article
em En
| MEDLINE
| ID: mdl-31793778
ABSTRACT
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.
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MEDLINE
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En
Ano de publicação:
2020
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Article