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Synfacts 2022; 18(12): 1386
DOI: 10.1055/s-0042-1752346
DOI: 10.1055/s-0042-1752346
Peptide Chemistry
Synthesis of N-Allyl Amino Acids and Peptides
Zumpe FL,
Kazmaier U.
*
Universität Heidelberg, Germany
Application of the Palladium-Catalyzed N-Allylation to the Modification of Amino Acids and Peptides.
Synthesis 1999; 1785-1791
DOI: 10.1055/s-1999-3598.
Application of the Palladium-Catalyzed N-Allylation to the Modification of Amino Acids and Peptides.
Synthesis 1999; 1785-1791
DOI: 10.1055/s-1999-3598.
Significance
N-Alkyl amino acids and peptides are key building blocks for many peptide drugs. In particular, N-allyl amino acids and peptides form key motifs for the synthesis of cyclic peptides. In 1999, Kazmaier and Zumpe developed a palladium-catalyzed N-allylation of N-tosyl and N-trifluoroacetyl amino acids and peptides.
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Comment
Palladium-catalyzed N-allylation of esters of N-tosyl and N-trifluoroacetyl amino acids and peptides with allyl ethyl carbonate proceeded smoothly to deliver desired products in good yields. The protocol is very simple in practice and proceeds under neutral conditions.
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Publication History
Article published online:
17 November 2022
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