Recent Advances of the Catalysis Systems in the α-C(sp3)—H Functionalization of Glycine Derivatives

doi:10.6023/cjoc202403004

Abstract

α-Amino acids are essential components of proteins, which are not only widely used in biologically active compound syntheses, medicinal chemistry, and the materials industry, but also are useful as organic catalysts or ligands for asymmetric synthesis. Glycines are the most fundamental and sole achiral α-amino acids, and are particularly useful building blocks in organic synthesis. Direct α-C(sp³)—H functionalization of glycine derivatives or peptides to construct unnatural α-amino acids or peptides has attracted tremendous attention of many scholars in recent decades. The research progress of the α-C(sp³)—H functionalization of glycine derivatives is reviewed during the past five years. The catalysis systems are systematically discussed, and the challenges and opportunities of this field are included.

Key words: a-amino acids, catalysis systems, C(sp³)—H functionalization, glycine, peptides

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Liangming Xuan, Wei Zhao, Rundong Fan, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances of the Catalysis Systems in the α-C(sp³)—H Functionalization of Glycine Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2700-2721.

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Fig. & Tab. 36

Scheme 1. α-C(sp3)—H bond activation of glycine derivatives

Scheme 2. Co-catalyzed α-C(sp3)—H oxidative coupling of glycine and peptide derivatives

Scheme 3. Copper-catalyzed double-oxidative dehydrogenative (DOD) [4＋2]-cyclization/oxidative aromatization tandem reaction of glycine derivatives with ethylbenzenes

Scheme 4. Copper-catalyzed aerobic oxidative dehydrogenative ring-opening reaction of glycine esters with α'-angelicalactone

Scheme 5. Transition-metal-catalyzed oxidative phosphonylation or cyclization of glycine derivatives

Scheme 6. Copper catalyzed cyanation of glycine derivatives

Scheme 7. Copper-catalyzed cyanoalkylation of glycine derivatives

Scheme 8. Iron-catalyzed radical cyclization/C(sp3)—H alkylation cascade between unsaturated oxime esters and glycine derivatives

Scheme 9. Fe-catalyzed C(sp3)—H methylation of glycine derivatives and peptides

Scheme 10. Cu-catalyzed three-component C—H trifluoroalkylation of glycine derivatives

Scheme 11. Fe-catalyzed oxidative tandem cyclization of glycine esters with propargyl alcohols

Scheme 12. Cu-catalyzed α-alkylation of glycine derivatives

Scheme 13. Visible-light-driven copper-catalyzed C(sp3)—H alkylation of glycine and peptides

Scheme 14. Visible-light-promoted C(sp3)—H alkylation of glycine and peptides with alkyl Katritzky salts

Scheme 15. Visible-light-driven copper-catalyzed radical cross-coupling of N?alkoxyphthalimides with amino acid esters

Scheme 16. Visible-light promoted α-alkylation of glycine derivatives with alkyl boronic acids

Scheme 17. Visible-light-induced oxidative cyclization of glycine derivatives

Scheme 18. Photocatalyzed oxidative tandem [4＋2] cyclization of glycine derivatives with maleimides

Scheme 19. Visible-light-driven copper-catalyzed C(sp3)—H dehydrogenative radical coupling of glycine derivatives

Scheme 20. Photoinduced palladium-catalyzed direct alkylation of glycine derivatives with alkyl bromides

Scheme 21. Visible light-induced C(sp3)—H functionalization of glycine derivatives with heterocyclic compounds

Scheme 22. Metal-free, visible-light-promoted oxidative radical cyclization of N-biarylglycine esters

Scheme 23. Visible light-induced oxidative dehydrogenative coupling reaction of glycine derivatives

Scheme 24. Visible-light driven C—H ketoalkylation of glycine derivatives and peptides

Scheme 25. Photoinduced radical-radical coupling of glycine de-rivatives with N-alkoxyphthalimides

Scheme 26. Visible-light driven α-C(sp3)—H gem-difluoroallylation of glycine derivatives with α-trifluoromethyl alkenes

Scheme 27. Photoinduced cross-dehydrogenative-coupling/cyclization reaction of glycine derivatives with o-hydroxyarylenaminones

Scheme 28. Photocatalyst- and additive-free C(sp3)—H hydrazination of glycine derivatives and peptides

Scheme 29. Oxidative dehydrogenative [2＋3] cyclization of glycine derivatives with aziridines

Scheme 30. Auto-oxidation promoted C(sp3)—H arylation of glycine derivatives

Scheme 31. Auto-oxidative Povarov/aromatization tandem reaction of glycine derivatives with enamides

Scheme 32. Catalyst- and additive-free α-alkylation reactions of glycine derivatives

Scheme 33. Asymmetric functionalization of glycine derivatives via visible-light-induced photoredox/Br?nsted acid catalysis

Scheme 34. Copper-catalyzed asymmetric C(sp3)—H alkylation of glycine derivatives and peptides

Scheme 35. Visible-light-induced copper-catalyzed asymmetric C(sp3)—C(sp3)—H glycosylation

Scheme 36. Copper-catalyzed asymmetric remote C(sp3)—H alkylation of N-fluorocarboxamides with glycine derivatives and peptides

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基于甘氨酸衍生物α-C(sp³)—H官能团化的催化体系研究进展

Recent Advances of the Catalysis Systems in the α-C(sp³)—H Functionalization of Glycine Derivatives

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基于甘氨酸衍生物α-C(sp3)—H官能团化的催化体系研究进展