手性季鏻盐促进不对称加成反应的最新进展

doi:10.6023/cjoc202502032

有机化学 ›› 2025, Vol. 45 ›› Issue (12): 4335-4345.DOI: 10.6023/cjoc202502032 上一篇下一篇

综述与进展

手性季鏻盐促进不对称加成反应的最新进展

张胜, 陈明, 张萌, 陈泠竹^*()

贵州大学绿色农药全国重点实验室贵阳 550025

收稿日期:2025-02-25 修回日期:2025-05-14 发布日期:2025-06-11
通讯作者: 陈泠竹
基金资助:
贵州省科学技术厅(黔科合基础[2024]青年136); 中央引导地方科技发展资金项目[黔科合中引地Nos. (2024)007, (2023)001]; 贵州大学高效低风险农药学科创新引智基地(111引智基地,No.D20023)

Recent Advances in Asymmetric Addition Reactions Promoted by Chiral Phosphonium Salts

Sheng Zhang, Ming Chen, Meng Zhang, Lingzhu Chen^*()

National Key Laboratory of Green Pesticide, Guizhou University, Guiyang 550025

Received:2025-02-25 Revised:2025-05-14 Published:2025-06-11
Contact: Lingzhu Chen
Supported by:
the Science and Technology Department of Guizhou Province(Qiankehejichu[2024]Youth136); Central Government Guides Local Science and Technology Development Fund Projects [Qiankehezhongyindi Nos. (2024)007, (2023)001]; Program of Introducing Talents of Discipline of the Pesticides with High Performance and Low Risks to Guizhou University (111 Talent Introducing Program,No.D20023)

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摘要/Abstract

手性季鏻盐作为不对称合成中的一类高效有机催化剂, 近年来得到了广泛的发展. 在手性鏻盐催化的碳原子立体中心、杂原子中心、轴向手性和平面手性的构建中, 不对称加成反应一直占据主导地位. 总结了手性鏻盐催化的不对称加成反应的最新进展.

关键词: 季磷离子对, 不对称催化, 加成反应, 功能分子合成

Chiral quaternary phosphonium salts have recently been extensively developed as robust organic catalysts for asymmetric synthesis. Asymmetric addition reactions have been dominating in the chiral phosphonium salt-catalyzed construction of stereogenic carbon centers, heteroatom centers, axes and planes. The recent achievements in the chiral phosphonium-catalyzed asymmetric addition reactions are summarized.

Key words: quaternary phosphonium ion pair, asymmetric catalysis, addition reaction, functional molecule synthesis

引用此文

张胜, 陈明, 张萌, 陈泠竹. 手性季鏻盐促进不对称加成反应的最新进展[J]. 有机化学, 2025, 45(12): 4335-4345.

Sheng Zhang, Ming Chen, Meng Zhang, Lingzhu Chen. Recent Advances in Asymmetric Addition Reactions Promoted by Chiral Phosphonium Salts[J]. Chinese Journal of Organic Chemistry, 2025, 45(12): 4335-4345.

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图/表 14

Figure 1. Chiral phosphonium salt catalysts involved in the text

Scheme 1. Chiral phosphonium-catalyzed cycloaddition reaction between nitroolefins and α-diazophosphonate

Scheme 2. Chiral phosphonium-catalyzed addition/oxidation reaction between oxa[5]helicenes and diarylphosphine oxides

Scheme 3. Chiral phosphonium-catalyzed addition/enone reaction between conjugated diene benzopyranone compound and phosphine oxide.

Scheme 4. Chiral phosphonium-catalyzed addition/enone reaction between 3-alkenyl-oxindoles and α-bromoketones

Scheme 5. Chiral phosphonium-catalyzed addition/sulfone reaction between vinylsulfone and phenylmethanol

Scheme 6. Chiral phosphonium-catalyzed addition/oxidation reaction of β,γ-unsaturated ketones.

Scheme 7. Chiral phosphonium-catalyzed addition/imine reaction between pyrazolinone imines and α-brominated ketones

Scheme 8. Chiral phosphonium-catalyzed addition/imine reaction between cyclic N-sulfonyl imines and secondary phosphine oxides

Scheme 9. Chiral phosphonium-catalyzed addition/addition to heteroatom reaction between cyclic ketones and phosphine oxides

Scheme 10. Chiral phosphonium-catalyzed addition/addition to heteroatom reaction between ethynyl ketones and phosphine oxides

Scheme 11. Chiral phosphonium-catalyzed addition/nucleophilic substitution between (o-hydroxy)aryl-alkene aldehydes and aromatic compounds

Scheme 12. Chiral phosphonium-catalyzed addition/nucleophilic substitution between prism-like cage molecules and phenols/thiols

Scheme 13. Chiral phosphonium-catalyzed asymmetric intramolecular ring expansion reaction of cyclic sulfoximines

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手性季鏻盐促进不对称加成反应的最新进展

Recent Advances in Asymmetric Addition Reactions Promoted by Chiral Phosphonium Salts

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