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

doi:10.1055/a-2284-9845

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(15): 2339-2346
DOI: 10.1055/a-2284-9845

paper

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

Autor*innen

Madala Hari Babu‡

^aCollege of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea
Eunbin Jang‡

^bCollege of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea
Hyesu Jang

^bCollege of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea
Sang Kyum Kim

^bCollege of Pharmacy, Chungnam National University, Daejeon 34134, Republic of Korea
Jaehoon Sim ∗

^aCollege of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea

^cDepartment of Regulatory Science, Graduate School, Kyung Hee University, Seoul 02447, Republic of Korea

^dInstitute of Regulatory Innovation through Science, Kyung Hee University, Seoul 02447, Republic of Korea

Abstract

Alle Artikel dieser Rubrik

Abstract

Oxidative α-C(sp³)–H alkylation of N-arylated glycine derivatives with 4-alkyldihydropyridine 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.

Key words

unnatural amino acids - photocatalysis - 4-alkyl-1,4-dihydropyridines - persulfate - peptides

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Referenzen

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