过渡金属催化1,3-二烯的不对称环化反应研究进展

doi:10.6023/cjoc202510004

摘要/Abstract

过渡金属催化的1,3-二烯不对称环化反应是构建手性环状分子的重要策略, 在天然产物、药物分子及功能材料的合成中具有广泛应用. 系统介绍了近年来该领域的研究进展, 重点围绕1,2-位和1,4-位环化两种模式, 详细讨论了Heck反应、C—H键活化、Wacker-type氧化以及π-Lewis碱催化等多种策略介导的串联环化反应. 这些方法能够高效、高对映选择性地构建五元到八元的多种环系, 并展现出良好的官能团兼容性和底物多样性. 尽管该领域已取得显著成果, 但仍面临机理不明确、底物普适性有限和手性控制不足等挑战. 未来需通过机理深入研究、新型廉价金属催化剂开发以及底物范围拓展, 进一步推动该类反应的发展与应用.

关键词: 过渡金属, 1,3-二烯, 不对称环化

Transition metal-catalyzed asymmetric cyclization reactions of 1,3-dienes represent a powerful strategy for the construction of chiral cyclic compounds, with broad applications in the synthesis of natural products, pharmaceuticals, and functional materials. The recent advances in this field are systematically reviewed, focusing on two major cyclization modes: 1,2- and 1,4-cyclication. Detailed discussions are provided, including Heck reactions, C—H bond activation, Wacker-type oxidations, and π-Lewis base catalysis. These methods enable efficient and highly enantioselective construction of various ring systems ranging from five to eight membered cycles, demonstrating good functional group compatibility and substrate diversity. Despite considerable advances, several challenges still persist, including ambiguous reaction mechanisms, narrow substrate scope, and poor stereocontrol. Future developments should focus on in-depth mechanistic elucidation, the design of economical metal catalysts, and the expansion of substrate generality to enhance the utility of these transformations.

Key words: transition metal, 1,3-diene, asymmetric cyclization

引用此文

沈国礼, 何玥, 景士文, 安子博, 徐丹丹. 过渡金属催化1,3-二烯的不对称环化反应研究进展[J]. 有机化学, 2026, 46(5): 1916-1938.

Guoli Shen, Yue He, Shiwen Jing, Zibo An, Dandan Xu. Research Progress on Transition Metal-Catalyzed Asymmetric Cyclization Reactions of 1,3-Dienes[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1916-1938.

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图/表 41

图式1. 过渡金属催化1,3-二烯的不对称环化反应(本综述框架)

Scheme 1. Transition metal-catalyzed asymmetric cyclization reactions of 1,3-dienes (framework of this review)

图式2. 过渡金属催化1,3-二烯的Heck/Tsuji-Trost环化反应

Scheme 2. Transition metal-catalyzed Heck/Tsuji-Trost cyclization reactions of 1,3-dienes

图式3. Pd催化1,3-二烯与芳基碘化物的Heck/Tsuji-Trost环化反应

Scheme 3. Pd-catalyzed Heck/Tsuji-Trost cyclization reaction of 1,3-dienes with aryl iodides

图式4. Pd催化1,3-二烯与2-芳基碘化物的不对称Heck/Tsuji-Trost环化反应

Scheme 4. Pd-catalyzed asymmetric Heck/Tsuji-Trost cyclization of 1,3-dienes with 2-iodoarenes

图式5. Pd催化1,3-二烯Heck/Tsuji-Trost构建螺环化合物

Scheme 5. Pd-catalyzed Heck/Tsuji-Trost cyclization of 1,3-dienes for the construction of spirocyclic compounds

图式6. Pd/Sadphos催化2-溴苯酚和1,3-二烯的不对称Heck/Tsuji−Trost环化反应

Scheme 6. Pd/Sadphos-catalyzed asymmetric Heck/Tsuji-Trost cyclization of 2-bromophenol with 1,3-dienes

图式7. Pd/Xu-Phos催化碘代烯丙醇和1,3-环己二烯的不对称Heck/Tsuji-Trost环化反应

Scheme 7. Pd/Sadphos-catalyzed asymmetric Heck/Tsuji-Trost cyclization of 1,3-cyclohexadienes with iodoallylic alcohols

图式8. Pd/手性阴离子催化不对称Heck/Tsuji-Trost环化反应

Scheme 8. Pd/Chiral anion catalyzed asymmetric Heck/Tsuji-Trost cyclization reaction

图式9. Pd催化苯并三氮唑与1,3-二烯的Heck/Tsuji-Trost环化反应

Scheme 9. Pd-catalyzed as Heck/Tsuji-Trost cyclization of 1,3-dienes with benzotriazoles

图式10. Pd催化卤代烷基胺与1,3-二烯的自由基-Heck/Tsuji-Trost环化反应

Scheme 10. Pd-catalyzed radical-relay Heck/Tsuji-Trost annulation of haloalkylamines with 1,3-dienes

图式11. Pd催化卤代酰胺与1,3-二烯的自由基-Heck/Tsuji-Trost环化反应

Scheme 11. Pd-catalyzed radical-relay Heck/Tsuji-Trost annulation of haloamides with 1,3-dienes

图式12. Pd催化吲哚与1,3-二烯的自由基-Heck/Tsuji-Trost环化反应

Scheme 12. Pd-catalyzed radical-relay Heck/Tsuji-Trost annulation of indoles with 1,3-dienes

图式13. 过渡金属催化1,3-二烯基于C—H键活化的环化反应

Scheme 13. Transition-metal-catalyzed annulation of 1,3-dienes via C—H activation

图式14. Pd(II)催化芳基脲与1,3-二烯的碳酰胺化环化反应

Scheme 14. Pd(II)-catalyzed cyclative carboamidation of arylureas with 1,3-dienes

图式15. Pd(II)催化吲哚与1,3-二烯的不对称C—H键活化环化反应

Scheme 15. Pd(II)-catalyzed asymmetric C—H activation annulation of indoles with 1,3-dienes

图式16. Pd(II)催化吲哚衍生物分子内C—H键活化的级联环化反应

Scheme 16. Pd(II)-catalyzed intramolecular cascade reaction of indole derivatives intiated by C—H activation

图式17. Rh(III)催化1,3-二烯基于C—H键活化的不对称环化反应

Scheme 17. Rh(III)-catalyzed enantioselective cyclization of 1,3-dienes via C—H activation

图式18. Ir(I)催化亚胺与1,3-二烯不对称C—H键活化环化反应

Scheme 18. Ir(I)-catalyzed asymmetric C—H activation/annulation of imines with 1,3-dienes

图式19. Sc催化亚胺与1,3-二烯不对称C—H键活化环化反应

Scheme 19. Sc-catalyzed asymmetric C—H activation/annulation of imines with 1,3-dienes

图式20. Pd(II)催化1,3-二烯的Wacker-type的环化反应

Scheme 20. Pd(II)-catalyzed Wacker-type cyclization of 1,3- dienes

图式21. Pd(II)催化1,3-二烯与脲的环化反应

Scheme 21. Pd(II)-catalyzed cyclization of 1,3-dienes with ureas

图式22. Pd(II)催化1,3-二烯与邻苯二胺的环化反应

Scheme 22. Pd(II)-catalyzed cyclization of 1,3-dienes with 1,2-diaminobenzene

图式23. Pd(II)催化1,3-二烯与脲的不对称环化反应

Scheme 23. Pd(II)-catalyzed asymmetric cyclization of 1,3-dienes with ureas

图式24. Pd(II)催化1,3-二烯与苯酚衍生物的不对称环化反应

Scheme 24. Pd(II)-catalyzed asymmetric cyclization of 1,3-dienes with phenols

图式25. Pd(0)-π-Lewis碱催化1,3-二烯的不对称环化反应

Scheme 25. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-dienes

图式26. Pd(0)-π-Lewis碱催化1,3-二烯与醛亚胺的不对称环化反应

Scheme 26. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-dienes with aldimines

图式27. Pd(0)-π-Lewis碱/胺接力催化1,3-二烯的不对称环化反应

Scheme 27. Asymmetric cyclization of 1,3-dienes enabled by Pd(0)-π-Lewis base/amine relay catalysis

图式28. Pd(0)-π-Lewis碱催化1,3-二烯与α-酮酰胺不对称环化反应

Scheme 28. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-dienes with α-ketoamides

图式29. Pd(0)-π-Lewis碱催化1,3-二烯与2-甲酰基苯硼酸的不对称环化反应

Scheme 29. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-dienes with 2-formylbenzeneboronic acids

图式30. Pd(0)-π-Lewis碱催化缺电子1,3-二烯与1-氮杂二烯的不对称环化反应

Scheme 30. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of electron-deficient 1,3-dienes with 1-azadienes

图式31. Pd(0)-π-Lewis碱催化1,3-环己二烯与1-氮杂二烯的不对称环化反应

Scheme 31. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-cyclohexadienes with 1-azadienes

图式32. Ni催化1,3-二烯与1,1-二氯烯烃的环化反应

Scheme 32. Ni-catalyzed cyclization of 1,3-dienes with 1,1-dichloroalkenes

图式33. Ni催化1,3-二烯与1,2-二氯烯烃的不对称环化反应

Scheme 33. Ni-catalyzed asymmetric cyclization of 1,3-dienes with 1,1-dichloroalkenes

图式34. Ni催化1,3-二烯与1,2-二氯硅烷的不对称环化反应

Scheme 34. Ni-catalyzed asymmetric cyclization of 1,3-dienes with 1,2-dichlordisilanes

图式35. Rh催化1,3-二烯与乙炔酸二酯的不对称环化反应

Scheme 35. Rh-catalyzed asymmetric cyclization of 1,3-dienes with dialkyl acetylenedicarboxylate

图式36. Co催化1,3-二烯与炔烃的不对称环化反应

Scheme 36. Co-catalyzed asymmetric cyclization of 1,3-dienes with alkynes

图式37. Pd(0)-π-Lewis碱催化1,3-二烯与N-CN亚胺的不对称环化反应

Scheme 37. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-dienes with N-CN-imines

图式38. Ni催化1,3-二烯与二氯二硅烷的不对称环化反应

Scheme 38. Ni-catalyzed asymmetric cyclization of 1,3-dienes with dichlorodisilanes

图式39. Ni催化1,3-二烯与氯硅烷的不对称还原[4＋2]环化反应

Scheme 39. Ni-catalyzed enantioselective reductive [4＋2] cyclization of 1,3-dienes with chlorosilanes

图式40. Fe催化1,3-二烯的不对称[4＋4]环化反应

Scheme 40. Fe-catalyzed asymmetric [4＋4] cyclization of 1,3-dienes

图式41. Pd(0)-π-Lewis碱催化1,3-二烯与氮杂二烯的不对称环化反应

Scheme 41. Pd(0)-π-Lewis base catalyzed asymmetric cyclization of 1,3-dienes with azadienes

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