通过环加成反应和串联反应构建桥环化合物的研究进展

doi:10.6023/cjoc202007045

摘要/Abstract

桥环化合物广泛存在于天然产物和具有重要生理活性的分子中, 在药物化学、天然产物化学、合成化学、材料化学及生命科学等领域具有重要的应用价值. 近年来, 经过广大化学工作者的不懈努力, 已发展了系列高效构建桥环化合物的新方法. 从环加成反应和串联反应两种策略出发, 详细介绍近五年来用于构建桥环化合物的方法及最新研究进展, 简要分析目前方法的优势及存在的问题, 以期为从事有机合成及相关领域的研究者提供有益借鉴和参考.

关键词: 桥环化合物, 环加成, 串联反应

Bridged rings are frequently encountered in natural products and biologically active molecules, which have significant application in the field of medicinal chemistry, natural product chemistry, synthetic chemistry, material chemistry and life science. In recent years, with the unremitting efforts of a large number of chemists, a series of new methods have been developed for the efficient synthesis of bridged compounds. The detailed synthetic methods to access bridged compounds in the past five years involving cycloadditions and cascade reactions are summarized, and the advantages and problems of the current methods are briefly analyzed, which would provide useful reference for the researchers engaged in organic synthesis and related fields.

Key words: Keywords bridged ring, cycloaddition, cascade reaction

引用此文

王乐乐, 张子莹, 韩华彬, 刘雄利, 卜站伟, 王琪琳. 通过环加成反应和串联反应构建桥环化合物的研究进展[J]. 有机化学, 2021, 41(1): 12-51.

Lele Wang, Ziying Zhang, Huabin Han, Xiongli Liu, Zhanwei Bu, Qilin Wang. Recent Advances in the Construction of Bridged Rings through Cycloadditions and Cascade Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 12-51.

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图/表 59

图1. 几种重要的含桥环骨架的天然产物及药物

Figure 1. Some important natural products and pharmaceuticals containing bridged rings

图式1. 色氨酸衍生物与硝基烯参与的不对称[3+2]环加成反应

Scheme 1. Asymmetric [3+2] cycloaddition of tryptophan deri- vatives with nitrostyrene

Scheme 2. 色氨酸衍生的亚胺叶立德与2-硝基苯并呋喃参与的不对称去芳构化的[3+2]环加成反应

. Asymmetric dearomative [3+2] cycloadditions of tryptophan-derived imine ylides with 2-nitrobenzofurans

Scheme 3. 双金属“接力”催化构建螺托品烷骨架氧化吲哚

. Bimetallic relay catalysis for the construction of spirotropanyl oxindoles

图式4. 环状亚胺叶立德的不对称[3+2]环加成反应构建氮杂双环[3.2.1]辛烷

Scheme 4. Asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides for the synthesis of chiral 8-azabicyclo[3.2.1]octanes

图式5. 三组分反应合成多取代的桥环四氢喹啉和二氢喹啉衍生物

Scheme 5. Three-component reactions ofN-alkylquinolinium salts for the synthesis of multisubstituted bridged tetrahydroquinolines and dihydroquinoline derivatives

图式6. 光催化亚胺与喹啉的[3+2]环加成反应

Scheme 6. Photocatalytic [3+2] cycloadditions of imines with quinolones

图式7. 光催化N-芳基-α-氨基酸与异喹啉氮氧化物参与的[3+2]环加成反应

Scheme 7. Photoredox-catalysed formal [3+2] cycloaddition involvingN-arylα-amino acids with isoquinolineN-oxides

图式8. Michael加成诱导的串联环化构建桥环O,O-/N,O-缩酮

Scheme 8. Michael addition-inspired cascade annulations for the construction of bridgedO,O-/N,O-ketals

图式9. 有机催化不对称合成具有螺环氧化吲哚骨架的桥环缩酮

Scheme 9. Organocatalytic asymmetric synthesis of bridged acetals with spirooxindole skeletons

Scheme 10. 指甲花酮与烷基乙烯基酮参与的不对称[3+2]环加成反应

. Asymmetric formal [3+2] cycloaddition of lawsones with alkyl vinyl ketones

图式11. 通过氧化偶联环化反应构建桥环双吲哚啉

Scheme 11. Construction of bridged bisindolines via oxidative coupling cyclization

Scheme 12. 芳香醛和亚胺叶立德参与的串联环化反应

. Cascade annulations of aromatic aldehydes and azomethine ylides

图式13. 不对称Michael加成/半缩酮化/氧杂-Pictet-Spengler串联反应构建螺环桥环氧化吲哚

Scheme 13. Asymmetric Michael addition/hemiketalization/oxa-Pictet-Spengler cascade for the synthesis of bridged spirooxindoles

Scheme 14. TfOH催化的Michael加成“诱导”的串联环化反应构建螺环桥环氧化吲哚

. A TfOH-catalyzed Michael addition-inspired cascade annulation for the construction of bridged spirooxindoles

图式15. 邻羟基肉桂醛与3-吲哚取代氧化吲哚参与的不对称Michael加成/半缩醛化/Friedel-Crafts烷基化串联反应

Scheme 15. Asymmetric Michael addition/hemiacetalization/Friedel-Crafts alkylation sequence of 2-hydroxy cinnamaldehydes and 3-indolyl oxindoles

Scheme 16. [3+3]环加成反应合成桥环黄酮类化合物

. Synthesis of bridged flavonoid derivatives via [3+3] cycloaddition

图式17. Sanctis A和Sanctis B的仿生全合成

Scheme 17. Biomimetic total syntheses of sanctis A and sanctis B

Scheme 18. 2-乙烯基吲哚与环状亚胺叶立德参与的不对称[3+3]环加成反应

. Asymmetric [3+3] annulation of 2-vinylindoles with cyclic azomethine ylides

图式19. 2,3-双取代的吲哚与烯丙基碳酸酯参与的[4+2]环加成反应

Scheme 19. Formal [4+2] cycloaddition of 2,3-disubstituted indoles with functionalized allylic carbonates

图式20. 2,3-双取代吲哚与邻氨基苄醇参与的[4+2]环加成反应

Scheme 20. [4+2] cycloaddition of 2,3-disubstituted indoles witho-aminobenzyl alcohols

Scheme 21. 吲哚和邻羟基查尔酮参与的多组分串联环化反应

. A multicomponent cascade reaction of indoles andortho-hydroxychalcones

图式22. 3-羟基吡喃酮与环戊烯二酮参与的不对称Diels-Alder反应

Scheme 22. Asymmetric Diels-Alder reaction of 3-hydroxypyrones with cyclopentendiones

Scheme 23. 吡喃酮和α,β-不饱和醛参与的不对称的[4+2]环加成反应

. Asymmetric [4+2] cycloadditions of pyrones andα,β-unsaturated aldehydes

图式24. 不对称Robinson环化反应制备手性桥连咔唑衍生物

Scheme 24. Asymmetric Robinson annulation for the construction of chiral bridged tricyclic hydrocarbazoles

图式25. N-烷基氧化吡啶盐与共轭二烯的[4+3]环加成反应

Scheme 25. [4+3] cycloaddition ofN-alkyl oxidopyridinium ions with conjugated dienes

图式26. 丙二烯酰胺和呋喃参与的不对称氧化/[4+3]环加成反应

Scheme 26. Asymmetric oxidative [4+3] cycloadditions between allenamides and furans

Scheme 27. 邻亚甲基醌参与的无金属催化[4+3]环加成反应

. Metal-free [4+3] cycloaddition ofortho-quinone methides

图式28. 双金属“接力”催化[4+3]环加成反应构建手性氧杂噁唑嗪桥环化合物

Scheme 28. Asymmetric synthesis of oxa-bridged oxazocines through a bimetallic relay [4+3] cycloaddition reaction

图式29. 羰基叶立德与邻亚甲基醌的不对称[4+3]环加成反应

Scheme 29. Asymmetric [4+3] cycloaddition of carbonyl ylides withortho-quinone methides

Scheme 30. 铑(III)催化2-芳基咪唑[1,2-a]吡啶与环己烯酮的串联环化反应

. Rh(III)-Catalyzed tandem bicyclization of 2-arylimidazo[1,2-a]pyridines with cyclohexanone

Scheme 31. α-溴代异羟肟酸与氨茴内酐参与的[4+3]环加成反应

. [4+3] cycloaddition ofα-bromohydroxamates with anthranils

图式32. [4+3]环加成反应合成环庚烷[b]吲哚

Scheme 32. Construction of cyclohepta[b]indoles through [4+3] cycloadditions

Scheme 33. 共催化剂控制多样性合成螺环O,O-缩酮和桥环O,O-缩酮 Cocatalyst-controlled diverse synthesis of spiro- and bridged-O,O-ketals

图式34. Type-II分子内[5+2]环加成反应

Scheme 34. Type-II intramolecular [5+2] cycloadditions

Scheme 35. 不对称去芳构化的[5+2]环加成反应构建托品烷衍生物

. Asymmetric dearomative [5+2] cycloadditions of isoquinolines to access tropane derivatives

图式36. 双金属“接力”催化策略: [5+2]环加成反应构建螺环桥环氧化吲哚

Scheme 36. Bimetallic relay catalysis: an approach to spiro-tropanyl oxindoles through [5+2] cycloadditions

图式37. 苯醌单缩酮和杂环烯酮缩胺的[5+3]环加成反应

Scheme 37. A [5+3] cycloaddition of quinone monoketals with heterocyclic ketene aminals

图式38. 2-芳基吲哚与苯醌单缩酮参与的[5+4]环加成反应

Scheme 38. [5+4] cycloadditions of 2-arylindoles with quinone monoacetals

图式39. 2-炔基N-炔丙基苯胺参与的串联环化反应构建桥环吲哚啉

Scheme 39. Cascade reaction of 2-alkynyl-N-propargylanilines to access bridged indolines

Scheme 40. 炔丙醇与2-乙烯基酚参与的串联环化反应

. A cascade annulation of propargylic alcohols with 2-vinylphenols

Scheme 41. 1,4-加成诱导的串联反应构建桥氧杂双环[3.3.1]壬烷

. Construction of dioxabicyclo[3.3.1]nonanes through 1,4-conjugate addition-inspired cascade reaction

Scheme 42. 硫杂橙酮衍生物与联烯酸酯参与的串联环化反应

. Cascade cyclizations of thioaurones and allenoate

Scheme 43. DABCO催化水杨酰腙与2-氧代3-丁炔酸酯的多级串联反应

. DABCO-Catalyzed cascade reactions of salicylhydrazones with 2-oxo-3-butynoates

图式44. Michael加成诱导的串联环化反应构建O,O-缩酮螺环桥环氧化吲哚

Scheme 44. Michael addition-triggered cascade annulations for the assembly of bridgedO,O-ketal spirooxindoles

Scheme 45. 底物控制的串联环化反应构建螺环桥环化合物和笼状桥环化合物

. Substrate-controlled cascade processes for the construction of spiro-bridged and cagelike bridged polyheterocycles

图式46. Fe(III)-催化的Friedel-Crafts烷基化/半缩酮化/内酯化串联反应构建桥环色满骨架化合物

Scheme 46. Fe(III)-catalyzed Friedel-Crafts alkylation/ hemiketalization/lactonization cascade reactions to access bridged chromans

图式47. [3+2]环加成/Stetter反应串联: 用于构建手性螺环桥环氧化吲哚

Scheme 47. A tandem [3+2] cycloaddition/Stetter reaction to construct chiral spiro-bridged oxindoles

Scheme 48. Mannich/Michael加成/aldol串联反应构建桥环四氢异喹啉

. A domino Mannich/Michael addition/aldol reaction for the construction of bridged tetrahydroisoquinones

图式49. 2-呋喃甲醇和胺参与的氮杂-Piancatelli环化/Michael加成串联反应

Scheme 49. Aza-Piancatelli cyclization/Michael addition sequence of 2-furylcarbinols and amines

Scheme 50. N-烷基氮杂芳烃盐反应位点的最大化利用

. Maximization of the reactive sites ofN-alkyl activated azaarenes

图式51. 反应可能的机理

Scheme 51. Plausible reaction mechanism

图式52. 通过原位活化去芳构化策略实现氮杂芳烃的多官能化

Scheme 52. Multifunctionalization of azaarenes throughin situactivation and sequential dearomatization

图式53. 新型N-查尔酮吡啶盐及其与烯胺酮的串联环化反应

Scheme 53. New chalcone-based pyridinium salts and their cascade annulations with enaminones

图式54. 环加成反应在天然产物Vocalgine A和Bipleiophylline中的应用

Scheme 54. Application of cycloaddition in total synthesis of vocalgine A and bipleiophylline

图式55. 取代吲哚与苯酚参与的氧化[3+2]环加成反应及其作为关键反应步骤合成phalarine

Scheme 55. Oxidative [3+2] cycloaddition of substituted indoles with phenols and its application as key step in the total synthesis of phalarine

Scheme 56. 不对称Michael加成/Aldol串联反应作为关键步骤合成(+)-tronocarpine

. Asymmetric Michael addition/aldol sequential process as key step to construct (+)-tronocarpine

图式57. 氮杂-频哪醇重排构建桥环吲哚啉和假吲哚

Scheme 57. Aza-pinacol rearrangement for the synthesis of bridged indolines and indolenine

Scheme 58. 氮杂频哪醇重排用于minfiensine的形式全合成

. Application of aza-pinacol rearrangement in the formal total synthesis of minfiensine

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