Synthesis of N-Allyl Amino Acids and Peptides

Key words

palladium catalysis - allylation - amino acids - peptides

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.

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.

Publication History

Article published online:
17 November 2022