钯催化烯烃的不对称氢酯基化反应研究进展

doi:10.6023/cjoc202509035

摘要/Abstract

不对称氢酯基化反应因其原子经济性和步骤简洁性, 已成为合成手性羧酸衍生物最具吸引力的途径之一. 该反应的核心挑战在于同时实现高化学、区域与对映体选择性的协同调控, 而手性配体作为催化体系的关键组分, 通过精准调控过渡金属活性中心的立体电子特性及配位环境, 可以直接主导反应的催化效率与立体化学调控. 本综述系统梳理了数十年来钯催化烯烃的不对称氢酯基化反应研究进展, 同时评述了手性配体的创新设计对选择性控制的突破性贡献, 并展望了该领域面临的挑战与未来发展方向.

关键词: 手性配体, 不对称, 氢酯基化, 钯催化

Asymmetric hydroesterification has become one of the most attractive pathways for synthesizing chiral carboxylic acid derivatives due to its atom economy and step simplicity. The core challenge of this reaction lies in the simultaneous achievement of synergistic control over high chemo-, regio-, and enantioselectivity. Chiral ligands, as key components of the catalytic system, directly govern the catalytic efficiency and stereochemical control of the reaction by precisely modulating the stereoelectronic properties and coordination environment of the transition metal active center. This review systematically summarizes the research progress over decades in palladium-catalyzed asymmetric hydroesterification of alkenes, critically evaluates the breakthrough contributions of innovative chiral ligand design to selectivity control, and discusses the challenges and future development directions in this field.

Key words: chiral ligands, asymmetric, hydroesterification, palladium-catalyzed

引用此文

冯凯, 贺兆波, 王震. 钯催化烯烃的不对称氢酯基化反应研究进展[J]. 有机化学, 2026, 46(5): 1897-1915.

Kai Feng, Zhaobo He, Zhen Wang. Recent Advances in Palladium-Catalyzed Asymmetric Hydroesterification of Alkenes[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1897-1915.

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图/表 28

图1. 不对称氢酯基化反应

Figure 1. Asymmetric hydroesterification reactions

图2. 苯乙烯的不对称氢酯基化反应研究进展

Figure 2. Research progress on asymmetric hydroesterification of styrene

图3. 手性催化剂在不对称氢酯基化反应中的应用

Figure 3. Application of chiral catalysts in asymmetric hydroesterification reactions

图4. 甲酸苯酯作为羰源合成2-芳基丙酸苯酯

Figure 4. Synthesis of 2-arylpropionic acid phenyl ester using phenyl formate as carbonyl source

图5. α-芳基丙烯酸的不对称氢酯基化反应

Figure 5. Asymmetric hydroesterification of α-aryl acrylic acid

图6. 环内烯烃的不对称氢酯基化反应

Figure 6. Asymmetric hydroesterification of intracyclic alkenes

图7. β-羰基辅助烯烃的不对称氢酯基化反应

Figure 7. β-Carbonyl-assisted asymmetric hydroesterification of alkenes

图8. 硫醇参与的共轭二烯的不对称氢酯基化反应

Figure 8. Thiol-involved asymmetric hydroesterification of conjugated dienes

图9. 硫醇参与的芳基乙烯的不对称氢酯基化反应

Figure 9. Thiol-involved asymmetric hydroesterification of aryl olefins

图10. 叔丁基硫醇参与的不对称氢酯基化反应

Figure 10. Asymmetric hydroesterification involving tert-butyl mercaptan

图11. 烯丙醇的氢酯基化反应

Figure 11. Hydroesterification of allylic alcohols

图12. 多取代烯丙醇与(－)-BPPM的不对称氢酯基化反应

Figure 12. Asymmetric hydroesterification of polysubstituted allylic alcohols with (－)-BPPM

图13. 多取代烯丙醇与BICP的不对称氢酯基化反应

Figure 13. Asymmetric hydroesterification of polysubstituted allylic alcohols with BICP

图14. 手性四氢呋喃稠合双环γ-内酯的合成

Figure 14. Synthesis of chiral THF-fused bicyclic γ-lactone

图15. 控制实验

Figure 15. Control experiments

图16. 烯丙醇与(S,S)-DIOP的不对称氢酯基化反应

Figure 16. Asymmetric hydroesterification of allylic alcohols with (S,S)-DIOP

图17. 烯基苯酚与甲酸苯酯的不对称氢酯基化反应

Figure 17. Asymmetric hydroesterification of alkenylphenols with phenyl formate

图18. 烯基苯酚与甲酸苯酯的不对称氢酯基化反应机理

Figure 18. Mechanism of asymmetric hydroesterification between alkenylphenols and phenyl formate

图19. 烯基苯酚与(R,R,R,R)-WingPhos的不对称氢酯基化反应

Figure 19. Asymmetric hydroesterification between alkenylphenols and (R,R,R,R)-WingPhos

图20. 三级醇的不对称氢酯基化反应

Figure 20. Asymmetric hydroesterification reaction of tertiary alcohols

图21. 氯化钯/氯化铜催化的不对称氢羧基化反应

Figure 21. Asymmetric hydrocarboxylation catalyzed by PdCl2/CuCl2

图22. 水溶性钯配合物催化的不对称氢羧化反应

Figure 22. Asymmetric hydrocarboxylation catalyzed by water-soluble palladium complexes

图23. 手性催化剂在不对称氢羧基化反应中的应用

Figure 23. Application of chiral catalysts in asymmetric hydrocarboxylation

图24. 手性螺环配体参与下的不对称氢羧基化反应

Figure 24. Asymmetric hydrocarboxylation reaction involving chiral spirocyclic ligand

图25. 不对称氢羧基化反应合成手性药物分子

Figure 25. Asymmetric hydrocarboxylation reaction for the synthesis of chiral drug molecules.

图26. 环状烯烃的不对称氢羧基化反应

Figure 26. Asymmetric hydrocarboxylation of cyclic olefins

图27. 辅助基团促进的不对称氢羧基化反应

Figure 27. Auxiliary group-promoted asymmetric hydrocarboxylation

图28. 钯接力催化炔烃不对称双氢羰基化反应

Figure 28. Palladium relay-catalyzed asymmetric double hydro-carbonylation of alkynes

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