一氧化碳参与β-内酰胺化合物合成的研究进展

doi:10.6023/cjoc202104060

摘要/Abstract

β-内酰胺类化合物是具有高生物活性及高应用价值的抗生素, 如何高效高选择性地设计、合成该类化合物一直是有机化学研究的热点问题. 由于其环状结构中具有羰基结构, 利用一氧化碳(CO)作为羰源与底物分子发生羰基化反应也发展成为合成β-内酰胺的有效方法. 通过该方法可以一步高效合成结构多样性且新颖的β-内酰胺化合物. 综述了近年来通过不同底物分子与CO发生羰基化反应构建β-内酰胺的研究进展, 并且对该方法存在的问题以及未来发展方向进行了展望.

关键词: β-内酰胺, 一氧化碳, 羰基化, 氮杂环丙烷, 烯酮

β-Lactam compounds are antibiotics with high biological activity and high application value. Design and synthesis of β-lactams with high efficiency and high selectivity have always been a hot issue in organic chemistry. Because of the carbonyl group in the ring structure, the carbonylation reaction between substrate and carbon monoxide (CO) has also developed into a new method for synthesis of β-lactams, which can be used to synthesize novel and diverse structures in one step. In this paper, the carbonylation of different substrates with CO to synthesize β-lactams in recent years is reviewed, and the existing problems and future development of this strategy are prospected.

Key words: β-lactams, carbon monoxide, carbonylation, aziridine, ketene

引用此文

王鹏, 杨妲, 刘欢. 一氧化碳参与β-内酰胺化合物合成的研究进展[J]. 有机化学, 2021, 41(9): 3448-3458.

Peng Wang, Da Yang, Huan Liu. Recent Advances on the Synthesis of β-Lactams by Involving Carbon Monoxide[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3448-3458.

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图/表 38

图式1. 过渡金属催化合成β-内酰胺

Scheme 1. Synthesis of β-lactams catalyzed by transition metal

图式2. 钴催化二氮杂环丙烷合成β-内酰胺

Scheme 2. Carbonylation of diaziridines to β-lactams catalyzed by Cobalt

图式3. 氮杂环丙烷区域选择性扩环合成β-内酰胺

Scheme 3. Regiospecific ring expansion of aziridines to β-lactams

图式4. 钯催化2-取代3-乙烯基氮丙啶类化合物羰基化合成3,4-二取代2-氮杂环丁酮衍生物

Scheme 4. Novel entry to 3,4-disubstituted 2-azetidinone derivative via Pd-assisted carbonylation of 2-substituted 3-vinyl- aziridine

图式5. 钯催化手性乙烯基氮丙啶转化为β-内酰胺

Scheme 5. Pd-catalyzed transformation of a chiral vinylaziridine to a β-lactams

图式6. 高度环张力反式双环β-内酰胺的首次合成

Scheme 6. First synthesis of highly strained trans-bicyclic β- lactams

图式7. 四羰基镍催化氮杂环丙烷“一锅法”合成β-内酰胺

Scheme 7. One-pot conversion of aziridine to β-lactam using Nickel tetracarbonyl

图式8. [Lewis acid]+[Co(CO)4]–催化环氧化合物羰基化制备β-内酰胺

Scheme 8. Carbonylation of epoxides to β-lactams using [Lewis acid]+[Co(CO)4]– complexes

图式9. 铑催化氮杂环丙烷羰基化合成β-内酰胺的理论研究

Scheme 9. Theoretical study of Rh(I) catalyzed carbonylative ring expansion of aziridines to β-lactams

图式10. 钯催化乙烯基氮杂环丙烷的羰基化反应立体选择性合成反式β-内酰胺

Scheme 10. Stereoselective synthesis of trans-β-lactams by Pd-catalyzed carbonylation of vinyl aziridines

图式11. 钴催化功能化氮杂环丙烷羰基化反应合成β-内酰胺

Scheme 11. Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks

图式12. 氮杂环丙烷羰基化反应合成β-内酰胺的反应机理

Scheme 12. Mechanism for carbonylation of aziridines to β-lactams

图式13. 钯催化烯丙基磷酸二乙酯的羰基化反应合成β-内酰胺

Scheme 13. Pd-catalyzed carbonylation of allyl diethyl phosphate for synthesis of β-lactams

图式14. 钯催化[2+2]羰基化环加成立体选择性合成烯基β-内酰胺

Scheme 14. The stereoselective synthesis of alkenyl-β-lactams by Pd-catalyzed [2+2] carbonylative cycloaddition

图式15. 多组分(亚胺、酸性氯化物和一氧化碳)合成β-内酰胺

Scheme 15. Multicomponent synthesis of β-lactams from imines, acid chloride and carbon monoxide

图式16. 高区域选择性合成3,4-二芳基β-内酰胺

Scheme 16. Stereoselective synthesis of 3,4-diaryl β-lactams

图式17. Pd2(dba)3催化CO与N-甲苯腙盐和亚胺的反应

Scheme 17. Pd2(dba)3-catalyzed reactions of CO with N-tosyl- hydrazone salts and imines

图式18. 钯/N-杂环卡宾配合物催化苄基氯代物与亚胺的羰基化反应合成β-内酰胺

Scheme 18. Pd/N-heterocyclic carbene-catalyzed carbonylation of substituted benzyl chlorides with imine to synthesize β-lactams

图式19. [1+1+2]反应合成手性β-内酰胺

Scheme 19. [1+1+2] reaction for the synthesis of chiral β- lactams

图式20. 烯酮类化合物合成β-内酰胺的反应机理

Scheme 20. Reaction mechanism of synthesis of β-lactams by involving ketenes: mechanistic proposal

图式21. M—C键与M=C键的羰基化过程合成β-内酰胺

Scheme 21. Carbonylation of M—C bond and M=C bond to synthesize β-lactams

图式22. 钴催化乙氧羰基烯酮类化合物合成β-内酰胺

Scheme 22. Synthesis of β-lactams derived from the ethoxycarbonyl ketenes catalyzed by cobalt

图式23. [CoII(Por)]催化α-重氮羰基化合物合成β-内酰胺

Scheme 23. [CoII(Por)]-catalyzed trans-selective β-lactams synthesis from α-diazocarbonyl compounds

图式24. 铑催化卡宾前体与N-苄烯甲胺合成β-内酰胺

Scheme 24. Rh catalyst screening for β-lactams synthesis from carbene precursor and N-benzylidenemethanamine

图式25. 对映选择性钯催化C(sp3)—H烷基化制备β-内酰胺

Scheme 25. Access to β-lactams by enantioselective Pd(0)- catalyzed C(sp3)—H alkylation

图式26. 钯催化C—H活化脂肪胺制备氮杂环类化合物

Scheme 26. Pd-catalyzed C—H activation of aliphatic amines to give strained nitrogen heterocycles

图式27. 钯催化C(sp3)—H键的氨甲酰化合成β-内酰胺

Scheme 27. Synthesis of β-lactams by Pd(0)-catalyzed C(sp3)—H carbamoylation

图式28. 钯催化脂肪胺β-C—H键的羰基化反应合成β-内酰胺

Scheme 28. Pd(II)-catalyzed carbonylation of β-C—H bonds in aliphatic amines to synthesize β-lactams

图式29. α-叔胺模块驱动钯催化脂肪胺β-C—H键的羰基化反应合成β-内酰胺

Scheme 29. α-Tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of methylene β-C—H bonds to synthesize β-lactams

图式30. C(sp3)—H键活化策略构建β-内酰胺的反应机理

Scheme 30. Synthesis of β-lactams by C(sp3)—H carbonylation: mechanistic proposal

图式31. β-内酰胺药物中间体的合成

Scheme 31. Synthesis of β-lactam skeleton medical intermediate

图式32. 通过2-溴丙烯胺合成β-内酰胺

Scheme 32. Synthesis of β-lactams from 2-bromopropenyl- amine

图式33. Rh催化炔丙基胺类衍生物硅烷羰基化制备α-甲硅烷-β-内酰胺

Scheme 33. Approach to α-silylmethylene-β-lactams via Rh- catalyzed silylcarbonylation of propargylamine derivatives

图式34. 钯/铑催化羰基化环化反应合成双环β-内酰胺

Scheme 34. Synthesis of bicyclic β-lactams via Pd/Rh-catalyzed carbonylative coupling and cyclization reactions

图式35. PdCl2催化炔丙基胺的高效转化对合成(E)-α-氯亚烷基-β-内酰胺

Scheme 35. PdCl2-catalyzed efficient transformation of propargylic amines to (E)-α-chloroalkylidene-β-lactams

图式36. 铑纳米颗粒催化剂催化β-内酰胺的合成

Scheme 33. Synthesis of β-lactams catalyzed by rhodium nanoparticles

图式37. 钯催化N-烯丙胺的氧化羰基化反应合成β-内酰胺

Scheme 37. Pd-catalyzed oxidative carbonylation of N-allyl- amines for the synthesis of β-lactams

图式38. 钯催化多组分法制备β-内酰胺

Scheme 38. Pd-catalyzed multicomponent approach to β-lactams

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