Recent Advances in the Construction of Bridged Rings through Cycloadditions and Cascade Reactions

doi:10.6023/cjoc202007045

Abstract

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

Cite this article

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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Fig. & Tab. 59

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

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

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

. Bimetallic relay catalysis for the construction of spirotropanyl oxindoles

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

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

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

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

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

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

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

Scheme 11. Construction of bridged bisindolines via oxidative coupling cyclization

. Cascade annulations of aromatic aldehydes and azomethine ylides

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

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

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

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

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

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

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

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

. A multicomponent cascade reaction of indoles andortho-hydroxychalcones

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

. A cascade annulation of propargylic alcohols with 2-vinylphenols

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

. Cascade cyclizations of thioaurones and allenoate

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

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

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

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

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

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

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

. Maximization of the reactive sites ofN-alkyl activated azaarenes

Scheme 51. Plausible reaction mechanism

Scheme 52. Multifunctionalization of azaarenes throughin situactivation and sequential dearomatization

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

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

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

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

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

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

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通过环加成反应和串联反应构建桥环化合物的研究进展