Photoredox Catalyzed Oxidative C-H Alkylation of Glycine Derivatives with 4-alkyl-1,4-dihydropyridines

Madala Hari Babu, Eunbin Jang, Hyesu Jang, Sang Kyum Kim, Jaehoon Sim

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Herein, oxidative α-C(sp3)-H alkylation of N-arylated glycine derivatives with 4-alkyl dihydropyridine derivatives (alkyl-DHPs) as versatile alkyl radical precursors has been developed. Utilizing visible light-driven photoredox catalysis and ammonium persulfate as an oxidizing agent, this methodology facilitates the site-selective alkylation of glycine derivatives, enabling the site selective alkylation of peptides. The reaction exhibits broad substrate scope, including various alkyl radicals and acid-labile functional groups. This approach expands the synthetic toolbox in peptide chemistry, offering a mild and efficient method for the synthesis of modified peptides.

Original languageEnglish
JournalSynthesis
DOIs
Publication statusAccepted/In press - 2024

Bibliographical note

Publisher Copyright:
© 2024 Georg Thieme Verlag. All rights reserved.

Keywords

  • 4-alkyl-1
  • 4-dihydropyridine
  • peptides
  • persulfate
  • photocatalysis
  • Unnatural amino acids

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