Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3183-3200.DOI: 10.6023/cjoc202208002 Previous Articles     Next Articles

Special Issue: 不对称催化专辑

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P-手性化合物的不对称催化合成研究进展

李晖a,*(), 殷亮b,*()   

  1. a 运城学院应用化学系 山西运城 044000
    b 中国科学院上海有机化学研究所 中国科学院天然产物有机合成化学重点实验室 上海 200032
  • 收稿日期:2022-08-01 修回日期:2022-09-09 发布日期:2022-11-02
  • 通讯作者: 李晖, 殷亮
  • 基金资助:
    山西省高等学校科技创新(2022L478); 山西省回国留学人员科研基金(2020-141); 运城学院院级项目(CY-2020022); 国家自然科学基金(21871287); 国家自然科学基金(21922114); 上海市科学技术委员会基金(20JC1417100); 上海市科学技术委员会基金(21XD1424800)

Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds

Hui Lia(), Liang Yinb()   

  1. a Department of Applied Chemistry, Yuncheng University, Yuncheng, Shanxi 044000
    b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2022-08-01 Revised:2022-09-09 Published:2022-11-02
  • Contact: Hui Li, Liang Yin
  • Supported by:
    Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi(2022L478); Grants from the Shanxi Scholarship Counil of China(2020-141); Research Project of Yuncheng University(CY-2020022); National Natural Science Foundation of China(21871287); National Natural Science Foundation of China(21922114); Science and Technology Commission of Shanghai Municipality(20JC1417100); Science and Technology Commission of Shanghai Municipality(21XD1424800)

P-Chiral compounds are a valuable class of privileged structures in pharmaceutically and biologically active compounds and also serve as powerful and versatile ligands or organocatalysts in asymmetric synthesis. Therefore, their asymmetric synthese has gained increasing attention in the past two decades. By means of kinetic resolution (KR) or dynamic kinetic resolution (DKR) strategy, racemic secondary phosphines, their borane-adducts or their oxides can be transformed to the associated compounds with P-chirality, which serves as a straightforward and efficient protocol to construct a P-chiral center. The recent achievements of the transition-metal-catalyzed asymmetric syntheses of P-chiral compounds based on KR and DKR of racemic secondary phosphines, their borane-adducts and their oxides in the past two decades are summarized. Meanwhile, arylation, addition to activated alkenes or alkynes, alkylation and other reactions are covered respectively based on the varied reaction partners. These reaction entails the formation of new P—C, P—O and P—N bonds in an asymmetric manner. What’s more, the transformation of prochiral primary phosphines to P-chiral secondary phosphines is mentioned in the miscellaneous reaction section.

Key words: P-chiral compounds, transition-metal-catalysis, asymmetric catalysis, kinetic resolution, dynamic kinetic resolution