Carboxylate-Directed Pd-Catalyzed β-C(sp3)–H Arylation of N-Methyl Alanine Derivatives for Diversification of Bioactive Peptides

Autor: Yeom, Suyeon, Kim, Do Young, Kim, Seungwoo, Gontala, Arjun, Park, Jimin, Lee, Yong Ho, Kim, Hak Joong
Zdroj: Organic Letters; December 2023, Vol. 25 Issue: 50 p9008-9013, 6p
Abstrakt: This study presents a Pd(II)-catalyzed method for the β-C(sp3)–H arylation of N-Cbz- or N-Fmoc-protected N-methyl alanines, providing ready access to building blocks for N-methylated peptide synthesis. For this transformation, the native carboxylate was exploited as the directing group, attributing its success to the use of a monoprotected amino-pyridine ligand. Its synthetic utility was demonstrated by facile generation of nine analogues of the naturally occurring N-methylated cyclic peptide cycloaspeptide A.
Databáze: Supplemental Index