Progress in Synthesis of Medium-Sized Ring Compounds Catalyzed by Organophosphine

doi:10.6023/cjoc202405021

Abstract

Medium-sized rings (7~11 membered ring) are a class of important skeleton in organic molecules, which are commonly found in drugs, pesticides and many biologically active natural products, and play essential roles in organic synthetic chemistry. Organo-catalysis is an important methodology for the synthesis of medium-sized ring compounds, among which, organophosphine catalysis has the advantages of low cost, environmental friendliness, and easy recycling, which provides an economical and efficient route for the synthesis of medium-sized ring compounds. Therefore, this field of research has received continuous and extensive attention in recent decades. In this review, the research progress on the organophosphine-catalyzed synthesis of medium-sized ring compounds is summarized, detailing the different types of reaction substrates, reaction mechanisms, etc.

Key words: organocatalysis, phosphine catalysts, annulation reaction, medium-sized ring compounds

Cite this article

Xuling Pan, You Huang. Progress in Synthesis of Medium-Sized Ring Compounds Catalyzed by Organophosphine[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3609-3620.

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Fig. & Tab. 38

Scheme 1. PPh3-catalyzed [3＋2] annulation reaction of unsubstituted allenoates and electron deficient olefins

Scheme 2. PPh3-catalyzed [2＋8] annulation reaction of unsubstituted allenoates/allenones and tropone

Scheme 3. PPh3-catalyzed [3＋4] annulation reaction of unsubstituted allenoates and 3-chromanone formaldehyde derivatives

Scheme 4. PPh3-catalyzed [3＋4] annulation reaction of unsubstituted allenoates and methyl coumalate

Scheme 5. PBu3-catalyzed [3＋4] annulation reaction of α-substituted allenoates and azomethine imines

Scheme 6. PCy3-catalyzed [3＋2＋3] annulation reaction of unsubstituted allenoates and azomethine imines

Scheme 7. P(NEt2)3-catalyzed [3＋2＋3] annulation reaction of unsubstituted allenoates and azomethine imines

Scheme 8. P(NEt2)3-catalyzed annulation reaction of unsubstituted allenoates

Scheme 9. PBu3-catalyzed [4＋3] annulation reaction of α-substituted allenoates and C,N-cyclic azomethine imines

Scheme 10. PPh3-catalyzed sequential annulation reaction of γ-methyl-substituted allenoates and o-hydroxybenzaldehyde- derived imines

Scheme 11. PPh3-catalyzed annulation reaction of β′-acetoxy- substituted allenoates and 2-acyl-3-methylacrylonitrile

Scheme 12. PBu3-catalyzed [4＋3] annulation reaction of α-substituted allenoates and C,N-cyclic aromatic azomethine imines

Scheme 13. Chiral phosphine-catalyzed [4＋3] annulation reaction of α-substituted allenoates and C,N-cyclic aromatic azomethine imines

Scheme 14. Chiral phosphine-catalyzed [4＋4] annulation reaction of α-substituted allenoates and α,β-unsaturated imines

Scheme 15. P(4-MeOC6H4)3-catalyzed sequential annulation reaction of unsubstituted allenoates and thioaurone derivatives

Scheme 16. PMe2Ph-catalyzed annulation reaction of γ-sub- stituted allenoates and heptafulvenes

Scheme 17. PPh3-catalyzed [4＋3] annulation reaction of β′-substituted allenoates and o-hydroxyactive imines

Scheme 18. Chiral phosphine-catalyzed [2＋8] annulation reaction of γ-substituted allenoates and azaheptafulvenes

Scheme 19. PPh3-catalyzed [4＋5] annulation reaction of β′-substituted allenoates and 1,5-dinucleophiles

Scheme 20. P(4-MeOC6H4)3-catalyzed [6＋1] annulation reaction of α-substituted allenoates and chromone carboxaldehyde

Scheme 21. P(4-MeOC6H4)3-catalyzed [4＋3] annulation reaction of β′-acetoxy-substituted allenoates and benzimidazole- derived 1C,3N-dinucleophiles

Scheme 22. PPh3-catalyzed [3＋6] annulation reaction of MBH derivatives and tropone

Scheme 23. PPh3-catalyzed [3＋4] annulation reaction of MBH carbonates and methyl coumalate

Scheme 24. P(4-MeC6H4)3-catalyzed [3＋4] annulation reaction of MBH carbonates and 1,4-dinucleophiles

Scheme 25. P(4-MeOC6H4)3-catalyzed [3＋4] annulation reaction of MBH carbonates and N-tosyl azadienes

Scheme 26. Solvent-controlled [3＋4] annulation reaction of MBH carbonates and benzothiophene derivatives

Scheme 27. Phosphine-catalyzed sequential annulation reaction of unmodified MBH alcohols and azomethine imines

Scheme 28. Catalysts-controlled [3＋4] annulation reaction of MBH carbonates and fluorinated imidoyl chlorides

Scheme 29. PPh3/Pd(0) co-catalyzed [3＋4] annulation reaction of MBH carbonates and vinyl benzoxazinanones

Scheme 30. PPh3-catalyzed [3＋6] annulation reaction of MBH carbonates and dicyanoheptafulvene

Scheme 31. Phosphine-catalyzed [3＋4] annulation reaction of MBH carbonates and dinucleophilic indole derivatives

Scheme 32. PBu3-catalyzed ring-opening rearrangement reactions of vinylcyclopropanes

Scheme 33. Chiral phosphine-catalyzed intramolecular MBH annulation reaction of ketoenone

Scheme 34. PBu3-catalyzed intramolecular MBH annulation reaction

Scheme 35. PPh3-catalyzed [2＋5] annulation reaction of alkynes and 1,5-dinucleophiles

Scheme 36. PPh3-catalyzed ring-expansion reactions of sulfamate-derived cyclic imines and acetylenedicarboxylates

Scheme 37. PPh3-catalyzed intramolecular annulation reaction of alkynyl hemiketals

Scheme 38. PPh2Et-catalyzed [3＋4] annulation reaction of ynones and 2-sulfonamidobenzaldehyes

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