Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds

doi:10.6023/cjoc202208002

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^,^*()

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 Li^a(), Liang Yin^b()

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

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Hui Li, Liang Yin. Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3183-3200.

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Fig. & Tab. 27

Figure 1. Tautomerism of secondary phosphine oxides

Scheme 1. Pd(II)-catalyzed asymmetric arylation of diarylphosphine oxides

Scheme 2. Pd(0)-catalyzed asymmetric arylation of alkylarylphosphine oxides

Scheme 3. Co(II)-catalyzed asymmetric addition of secondary phosphine oxides to activated alkenes

Scheme 4. Pd(0)-catalyzed asymmetric hydrophosphinylation of alkylarylphosphine oxides

Scheme 5. Pd(0)-catalyzed asymmetric hydrophosphorylation of aryl phosphinates

Scheme 6. Ni(II)-catalyzed asymmetric allylation and benzylation

Scheme 7. Pd(0)-catalyzed asymmetric benzylation of alkylarylphosphine oxides

Scheme 8. Co(II)-catalyzed asymmetric alkylation of secondary phosphine oxides

Figure 2. Racemization of the metal-phosphido species derived from secondary phosphines

Scheme 9. Pd and Pt-catalyzed asymmetric arylation of secondary phosphines and their borane complexes

Scheme 10. Pd-catalyzed asymmetric arylation of secondary phosphines and silylphosphines

Scheme 11. Cu(II)-catalyzed asymmetric arylation of alkylarylphosphine oxides with diaryliodonium salts

Scheme 12. Palladacycle-catalyzed asymmetric 1,4-addition of methylphenylphosphine to enones

Scheme 13. Pincer Pd-catalyzed asymmetric hydrophosphination

Scheme 14. Cu(I)-Catalyzed asymmetric hydrophosphination of α,β-unsaturated amides

Scheme 15. Cu(I)-catalyzed asymmetric hydrophosphination of α,β-unsaturated phosphine sulfides

Scheme 16. Ni(II)-catalyzed asymmetric hydrophosphination of alkynes

Scheme 17. Ru(II)-catalyzed asymmetric alkylation

Scheme 18. Pt-Catalyzed asymmetric arylation

Scheme 19. Pincer Pd-catalyzed asymmetric alkylation

Scheme 20. Cu(I)-catalyzed asymmetric alkylation

Scheme 21. Ni(II)-catalyzed asymmetric allylation of secondary phosphine oxidates

Scheme 22. Pd-catalyzed asymmetric 1,6-addition of 2,5-diphenylbenzoquinones

Scheme 23. Pd-catalyzed asymmetric hydrazonation

Scheme 24. Cu(I)-catalyzed asymmetric amination

Scheme 25. Ni(II)-catalyzed asymmetric hydrophosphination of primary phosphines

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P-手性化合物的不对称催化合成研究进展

Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds

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Fig. & Tab. 27

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