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

doi:10.6023/cjoc202403004

摘要/Abstract

α-氨基酸是组成蛋白质的基本结构单元, 应用范围非常广泛, 它不仅能用于许多生物活性分子的合成、药物化学和材料工业中, 还可作为有机催化剂或配体用于各类化合物的不对称合成中. 甘氨酸作为最普遍且具有潜手性的α-氨基酸, 在有机合成领域是一类非常重要的合成砌块, 利用甘氨酸衍生物或多肽的α-C(sp³)—H官能团化, 高效构建结构多样性的非天然α-氨基酸或多肽引起了越来越多科研工作者的关注. 对近五年来甘氨酸衍生物α-C(sp³)—H官能团化领域所取得的研究进展进行了综述, 根据不同类型的催化体系进行了分类讨论, 并对该领域所面临的挑战和机遇进行了展望和探讨.

关键词: α-氨基酸, 催化体系, C(sp³)—H官能团化, 甘氨酸, 多肽

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

引用此文

宣良明, 赵伟, 范润东, 严琼姣, 汪伟, 陈芬儿. 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[J]. 有机化学, 2024, 44(9): 2700-2721.

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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图/表 36

图式1. 甘氨酸衍生物α-C(sp3)—H键活化

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

图式2. 钴催化甘氨酸及多肽的α-C(sp3)—H氧化偶联反应

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

图式3. 铜催化甘氨酸衍生物和乙基苯的双氧化去氢[4＋2]环化/氧化芳构化串联反应

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

图式4. 铜催化甘氨酸酯与α'-当归内酯的氧化脱氢开环反应

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

图式5. 过渡金属催化甘氨酸衍生物的膦酰化或氧化环化反应

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

图式6. 铜催化甘氨酸衍生物的氰基化反应

Scheme 6. Copper catalyzed cyanation of glycine derivatives

图式7. 铜催化的甘氨酸衍生物的C(sp3)—H氰烷基化反应

Scheme 7. Copper-catalyzed cyanoalkylation of glycine derivatives

图式8. 铁催化不饱和肟酯和甘氨酸衍生物的自由基环化/C(sp3)—H烷基化串联反应

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

图式9. 铁催化甘氨酸衍生物和多肽的C(sp3)—H甲基化反应

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

图式10. 铜催化的甘氨酸衍生物的三组分C—H三氟烷基化反应

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

图式11. 铁催化甘氨酸酯与炔丙醇的氧化串联环化

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

图式12. 铜催化甘氨酸衍生物的α-烷基化反应

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

图式13. 可见光促进铜催化的甘氨酸及多肽的C(sp3)—H烷基化

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

图式14. 可见光促进甘氨酸及多肽与Katritzky盐的C(sp3)—H烷基化反应

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

图式15. 可见光促进铜催化N-烷氧基邻苯二甲酰亚胺与氨基酸酯的自由基交叉偶联反应

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

图式16. 可见光促进甘氨酸衍生物与烷基硼酸的α-烷基化反应

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

图式17. 可见光促进甘氨酸衍生物的氧化环化反应

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

图式18. 光催化甘氨酸衍生物和马来酰亚胺的氧化串联[4＋2]环化反应

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

图式19. 可见光促进铜催化甘氨酸衍生物的C(sp3)—H交叉脱氢偶联

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

图式20. 光诱导促进钯催化甘氨酸衍生物与溴代烷基的直接烷基化

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

图式21. 可见光促进的甘氨酸衍生物与杂环化合物的C(sp3)—H官能团化

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

图式22. 无金属可见光促进N-联芳基甘氨酸酯的氧化自由基环化反应

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

图式23. 可见光促进的甘氨酸衍生物的脱氢偶联反应

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

图式24. 可见光驱动的甘氨酸衍生物和多肽的C—H酮烷基化

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

图式25. 可见光促进的甘氨酸衍生物与N-烷氧基邻苯二甲酰亚胺的自由基偶联反应

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

图式26. 可见光促进的甘氨酸衍生物与α-三氟甲基烯烃偕二氟烯丙基化反应

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

图式27. 可见光促进甘氨酸衍生物与邻羟基芳香胺的交叉脱氢偶联环化反应

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

图式28. 无光敏剂和添加剂光催化甘氨酸衍生物和多肽的C(sp3)—H肼化反应

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

图式29. 甘氨酸衍生物与氮杂环丙烷的氧化脱氢[2＋3]环化反应

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

图式30. 自氧化促进甘氨酸衍生物的C(sp3)—H芳基化

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

图式31. 甘氨酸衍生物与烯酰胺的自氧化Povarov/芳构化串联反应

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

图式32. 无催化剂和无添加剂甘氨酸衍生物的α-烷基化反应

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

图式33. 光氧化还原和布伦斯特酸协同催化甘氨酸衍生物的不对称官能团化反应

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

图式34. 铜催化甘氨酸衍生物及多肽的不对称C(sp3)—H烷基化反应

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

图式35. 可见光促进铜催化不对称C(sp3)—C(sp3)—H糖基化反应

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

图式36. 铜催化N-氟代酰胺和甘氨酸衍生物的远端C(sp3)—H不对称烷基化反应

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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