Regiocontrollable Difunctionalization of N-Allenamines

doi:10.6023/cjoc202309006

Abstract

As an electron-rich diene compound, N-allenamine has received wide spread attention in recent years due to its different reaction sites and high reactivity. Efficient and controllable regioselective functionalization of N-allenamines can successfully construct functionalized molecules. The research progress in the field of regioselective bifunctionalization of N-allenamines in recent years is mainly discussed, and the reaction mechanisms of most conversions in detail are discussed.

Key words: N-allenamine, regioselectivity, difunctionalization

Cite this article

Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.

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Fig. & Tab. 38

Scheme 1. Regioselectivity conversion of N-allenamide

Scheme 2. Stereoselective [2＋2] cycloaddition of allenes toward alkenes and alkynes

Scheme 3. Stereoselective intramolecular [4＋3] cycloadditions of N-allenamides

Scheme 4. Thermal intramolecular [4＋2] cycloadditions of N- allenamides

Scheme 5. Asymmetric intermolecular[4＋2] cycloadditions of N-allenamides and diene

Scheme 6. Gold-catalyzed intermolecular cyclization of ethenyl indole derivatives and N-allenamide

Scheme 7. Intermolecular [2＋2] and [4＋2] cyclization of 3- styrylindoles with N-allenamides

Scheme 8. Au(I)-catalyzed cycloaddition of allenamides with α,β-unsaturated hydrazones

Scheme 9. Enantioselective [2＋2] cycloaddition between indoles and N-allenamides

Scheme 10. Gold-catalyzed regiodivergent [2＋2＋2] cycloadditions of allenes with triazines

Scheme 11. Gold-catalyzed [2＋2＋2＋2] annulation of 1,3,5- hexahydro-1,3,5-triazines with N-allenamides

Scheme 12. [2＋2] and [4＋2] cycloadditions of phenylacetylene and cyclopentadiene with N-allenamides

Scheme 13. [5＋2] cycloaddition of quinolinium zwitterions and N-allenamides

Scheme 14. Annulations between allenes and alkene-tethered oxime ethers

Scheme 15. Cascade reactions of 4H-furo[2-b]indoles with N-allenamides

Scheme 16. Gold-catalyzed [4＋2＋2]-cycloaddition of anthranils with N-allenamides

Scheme 17. Palladium-catalyzed N-allenamide carbopalladation/allylation with active methine compounds

Scheme 18. Cyanoesterification of 1,2-dienes catalyzed by nickel

Scheme 19. Nickel-catalyzed arylation and methylation of N- allenamides via coupling reactions

Scheme 20. Intermolecular iodofunctionalization of N-allen- amides

Scheme 21. Lewis acid-catalyzed nucleophilic addition with silylated nucleophiles

Scheme 22. Gold-catalyzed 1,2-oxyalkynylation of N-allena- mides with ethylnylbenziodoxolones

Scheme 23. Copper-catalyzed difunctionalization of allenes with sulfonyl iodides

Scheme 24. Stereoselective [4＋2] cycloaddition reactions of chiral N-allenamides with heterodienes

Scheme 25. Acid-catalyzed cyclization of acyliminium ions derived from N-allenamides

Scheme 26. Cyclization of N-Boc-protected N-allenamides

Scheme 27. Intermolecular [2＋2] and [4＋2] cycloadditions of 3-styrylindoles with N-allenamides

Scheme 28. Intermolecular annulations with N-allenamides at the proximal C=C Bond

Scheme 29. [3＋2] carbocycloaddition reaction of vinyldiazo compounds and N-allenamides

Scheme 30. Intramolecular [2＋2] cycloaddition of N-allena- mide

Scheme 31. Gold-catalyzed asymmetric intramolecular cyclization of N-allenamides

Scheme 32. Rhodium-catalyzed [2＋2] cycloaddition of N- allenamide

Scheme 33. Enantioselective cyclization reaction of benzotriazoles with N-allenamides

Scheme 34. Palladium-catalyzed proximal addition of N-allen- amides

Scheme 35. Copper-catalyzed regioselective oxytrifluoromethylation

Scheme 36. Metal-free C—H functionalization of N-allena- mides

Scheme 37. Gold-catalyzed highly diastereoselective oxy-pro- pargylamination of N-allenamides

Scheme 38. Photoredox-catalyzed intermolecular radical addition of N-allenamides

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