Recent Advances in Asymmetric Addition Reactions Promoted by Chiral Phosphonium Salts

doi:10.6023/cjoc202502032

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (12): 4335-4345.DOI: 10.6023/cjoc202502032 Previous Articles Next Articles

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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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Abstract

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

Cite this article

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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Fig. & Tab. 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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