N-乙烯基酰胺参与的环化反应研究进展

doi:10.6023/cjoc202604012

摘要/Abstract

N-乙烯基酰胺是一类重要的有机合成中间体, 被广泛应用于有机合成中. 其结构独特、反应活性强、反应途径多样, 成为构建环状骨架的理想底物之一. 系统综述了N-乙烯基酰胺参与的环化反应来构建氨基环丙烷、噁唑啉、噁唑、吡啶等环状化合物的研究进展, 并详细阐述了各类反应体系的反应机理、底物适用范围、立体选择性调控以及产物应用价值.

关键词: 烯酰胺, 环化反应, 氨基环丙烷, 杂环化合物, 立体选择性

N-Vinylamides are an important class of synthetic building blocks, which are widely used in organic synthesis. Their unique structure, strong reactivity, and diverse reaction pathways make them ideal substrates for constructing cyclic frameworks. This review summarizes the recent progresses on cyclization reactions involving N-vinylamides to construct aminocyclopropanes, oxazolines, oxazoles, pyridines, and other cyclic compounds. The reaction mechanisms, substrate scope, stereoselectivity control, and the application of the products are also discussed.

Key words: enamide, cyclization reaction, aminocyclopropane, heterocyclic compounds, stereoselectivity

引用此文

邵长卿, 林凯贤, 熊毅, 何晓雨, 邹有全. N-乙烯基酰胺参与的环化反应研究进展[J]. 有机化学, 2026, 46(10): 3865-3888.

Changqing Shao, Kaixian Lin, Yi Xiong, Xiaoyu He, Youquan Zou. Recent Advances in Cyclization Reactions Using N-Vinylamides[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 3865-3888.

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图/表 51

图式1. (a)烯酰胺的共振式和反应位点; (b)代表性含氨基环丙烷或氮杂环的药物; (c)烯酰胺参与的环化反应

Scheme 1. (a) Enamides: resonance formula and its reaction site; (b) Representative drugs containing aminocyclopropane or N-contain-ing heterocycles; (c) Cyclization reactions of N-vinylamides

图式2. 手性烯酰胺的立体选择性Simmons-Smith环丙烷化反应

Scheme 2. Stereoselective Simmons-Smith cyclopropanation of chiral enamides

图式3. 铑催化手性烯酰胺π面选择性环丙烷化反应

Scheme 3. Ru(II) catalyzed π-facial selective cyclopropanation of chiral enamides

图式4. 钌催化烯酰胺的不对称环丙烷化反应

Scheme 4. Ru(II)-catalyzed asymmetric cyclopropanation of enamides

图式5. 钌催化N-乙烯基嘧啶的不对称环丙烷化反应

Scheme 5. Ru(II)-catalyzed asymmetric cyclopropanation of N-vinylpyrimidines

图式6. 铑催化N-乙烯基嘧啶的不对称环丙烷化反应

Scheme 6. Rh(II)-catalyzed asymmetric cyclopropanation of N-vinylpyrimidines

图式7. 钯催化烯酰胺氧化环丙烷化反应

Scheme 7. Pd-catalyzed oxidative cyclopropanation of enamides

图式8. 金催化烯酰胺的对映选择性环丙烷化反应

Scheme 8. The Au-catalyzed enantioselective cyclopropanation of enamides

图式9. 铑催化烯酰胺的不对称环丙烷化反应

Scheme 9. Rh(I)-catalyzed asymmetric cyclopropanation of enamides

图式10. 光催化烯酰胺的分子内环化反应

Scheme 10. Photocatalytic intramolecular cyclization of enamides

图式11. N-乙烯基酰胺和1,1-二溴甲醛肟的[3＋2]环化反应

Scheme 11. [3＋2] cycloaddition of N-vinylamide and 1,1-dibromoformylamine

图式12. N-乙烯基酰胺和硫叶立德的[4＋1]环化反应

Scheme 12. [4＋1] cycloaddition of N-vinylamides and sulfur ylides

图式13. 银催化的N-乙烯基酰胺和硫叶立德的[4＋1]环化反应

Scheme 13. Ag-catalyzed [4＋1] cycloaddition of N-vinylamides and sulfur ylides

图式14. IPCT诱导的可见光催化的烯酰胺环化反应

Scheme 14. IPCT-induced visible-light-catalyzed cyclization of N-vinylamides

图式15. 电催化烯酰胺的环化反应

Scheme 15. Electrocatalytic cyclization of enamides

图式16. 烯酰胺的环化反应用于构建含有噁唑骨架的天然产物

Scheme 16. Cyclization reactions of enamides for the construction of oxazole-containing natural products

图式17. 醋酸碘苯介导的烯酰胺分子内环化反应

Scheme 17. PIDA-mediated intramolecular cyclization of enamides

图式18. 高价碘介导的烯酰胺环化反应

Scheme 18. Hypervalent I-mediated cyclization of enamides

图式19. 碳酸银促进的烯酰胺环化反应

Scheme 19. Ag2CO3-mediated cyclization of enamides

图式20. 三氟乙酸介导的烯酰胺环化反应

Scheme 20. TFA-mediated cyclization of enamides

图式21. NBS/Me2S参与烯酰胺加热环化反应

Scheme 21. NBS/Me2S-participated thermal cyclization of enamides

图式22. 烯酰胺与氟烷基卤化物的脱氟环化反应

Scheme 22. Defluorinative cyclization of enamides with fluoroalkyl halides

图式23. β,β-二溴代烯酰胺在碱促进下的热环化脱溴反应

Scheme 23. Dase-promoted thermal cyclodebromination of β,β-dibrominated enamides

图式24. 铜催化烯酰胺分子内环化反应

Scheme 24. Cu-catalyzed intramolecular cyclization of enamides

图式25. 钯催化烯酰胺环化反应

Scheme 25. Pd-catalyzed cyclization of enamides

图式26. 光催化烯酰胺分子内环化反应

Scheme 26. Photocatalytic intramolecular cyclization of enamides

图式27. 铼催化烯酰胺与炔烃的环化反应

Scheme 27. The Re-catalyzed cycloaddition of enamides with alkynes

图式28. 钌催化烯酰胺与炔烃的环化反应

Scheme 28. The Ru-catalyzed cycloaddition of enamides with alkynes

图式29. 铜催化烯酰胺与磺酰肼的环化反应

Scheme 29. The Cu(II)-catalyzed cyclization of enamides with sulfonylhydrazide

图式30. 一价铜催化烯酰胺与炔烃的环化反应

Scheme 30. Cu(I)-catalyzed cycloaddition of enamides with alkynes

图式31. 铬催化烯酰胺分子内环化反应

Scheme 31. Cr-catalyzed intramolecular cyclization of enamides

图式32. 铑催化烯酰胺与炔烃的环化反应

Scheme 32. Rh-catalyzed cycloaddition of enamides with alkynes

图式33. 钌催化烯酰胺与炔烃的环化反应

Scheme 33. Ru-catalyzed cycloaddition of enamides with alkynes

图式34. 铜催化烯酰胺的环化反应

Scheme 34. Cu-catalyzed cyclization of enamides

图式35. 电催化烯酰胺的环化反应

Scheme 35. Electrocatalytic cyclization of enamides

图式36. 钛催化烯酰胺的环化反应

Scheme 36. Ti-catalyzed cyclization of enamides

图式37. 钯催化烯酰胺羰基化反应

Scheme 37. Pd-catalyzed carbonylation of enamides

图式38. 钯光协同催化烯酰胺的羰基化反应

Scheme 38. Pd with photoredox-catalyzed carbonylation of ena-mides

图式39. 无过渡金属参与的烯酰胺羰基化反应

Scheme 39. Ttransition-metal-free carbonylation of enamides

图式40. 二氧化碳参与的烯酰胺羰基化反应

Scheme 40. CO2-involved carbonylation of enamides

图式41. 铜催化烯酰胺与二氟卡宾前体羰基化反应

Scheme 41. The Cu-catalyzed carbonylation of enamides with difluorocarbene precursors

图式42. 金催化烯酰胺分子环化反应

Scheme 42. Au-catalyzed intramolecular cycloaddition of enamides

图式43. 铜催化烯酰胺与磺酰氯的环化反应

Scheme 43. Cu-catalyzed cyclization of enamides with sulfonyl chlorides

图式44. 无金属参与烯酰胺的三组分环化反应

Scheme 44. Metal-free three-component cyclization of enamides

图式45. 铜催化烯酰胺的三组分环化反应

Scheme 45. Cu-catalyzed three-component cyclization of enamides

图式46. 铑催化烯酰胺的[4＋2]环化反应

Scheme 46. Rh(III)-catalyzed [4＋2] cycloaddition of enamides

图式47. 三氟化硼乙醚催化的烯酰胺与醛的多米诺反应

Scheme 47. BF3•Et2O-catalyzed domino reaction of enamides with aldehydes

图式48. 钌催化烯酰胺与芳香异羟肟酸酯的环化反应

Scheme 48. Ru-catalyzed cycloaddition of enamides and aromatic hydroxamic acid esters

图式49. 碱促进烯酰胺与邻苯二胺的缩合环化反应

Scheme 49. Base-promoted condensative cycloaddition of enamides with o-phenylenediamine

图式50. 手性膦酸催化烯酰胺不对称环反应

Scheme 50. CPA-catalyzed asymmetric cycloaddition of enamides

图式51. 铁催化烯酰胺与二硒醚的环化反应

Scheme 51. Fe(III)-catalyzed cyclization of enamides with diselenides

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