铜催化的手性膦化合物不对称合成研究进展

doi:10.6023/cjoc202405002

有机化学

综述与进展

铜催化的手性膦化合物不对称合成研究进展

李晖^*,a, 殷亮^*,b

^a运城学院应用化学系运城 044000;
^b中国科学院上海有机化学研究所先进氟氮材料重点实验室上海 200032

收稿日期:2024-05-05 修回日期:2024-06-11
基金资助:
山西省高等学校科技创新(No. 2022L478), 山西省基础研究计划(No. 202303021211189)资助项目.

Research Progress on Copper-Catalyzed Asymmetric Synthesis of Chiral Organophosphorus Compounds

Hui Li^*,a, Liang Yin^*,b

^aDepartment of Applied Chemistry, Yuncheng University, Yuncheng, 044000;
^bKey Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

Received:2024-05-05 Revised:2024-06-11
Contact: *E-mail: lihuiwf@ycu.edu.cn; liangyin@sioc.ac.cn
Supported by:
Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (No. 2022L478), Natural Science Foundation of Shanxi province, China (No. 202303021211189).

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摘要/Abstract

手性含磷有机化合物在医药、农药、功能材料等领域具有广泛的应用, 还可用作不对称催化中的手性配体和有机小分子催化剂. 因此, 手性膦化合物的不对称合成受到合成化学家们的重视. 利用P—H化合物立体选择性地构建P—C键和P—N键等是合成手性膦化合物最直接且最有效的方法之一. 此综述着重介绍了铜在手性配体或手性有机小分子催化剂参与下高效构建手性膦化合物方面的研究进展. 根据铜催化剂在反应过程中价态是否发生改变, 将反应分为变价催化反应和非变价催化反应, 反应生成了P-手性、碳骨架手性或兼具P-手性和碳骨架手性的膦化合物. 同时, 对一些代表性的反应机理和产物应用也做了介绍.

关键词: 铜催化, 不对称催化, 手性膦化合物, P-手性

Chiral organophosphorus compounds have a wide range of application in the fields of medicine, pesticides, and functional materials, and also serve as versatile ligands or organocatalysts in asymmetric catalysis. Therefore, their asymmetric synthesis has attracted an increasing attention from chemists and has become one hot research topic in recent years. Asymmetric P—C or P—N bond formation by using organophosphorus compounds bearing P—H bond and various electrophilic partners serves as a straightforward and powerful strategy for constructing chiral organophosphorus compounds. Recent progress in asymmetric synthesis of chiral organophosphorus compounds catalyzed by chiral copper complexes or copper/organocatalyst co-catalytic systems is summarized. P-chiral or/and backbone chiral organophosphorus compounds are obtained in these reactions. This paper is divided into two sections based on whether the valence state of copper is changed or not during the reaction process. Aside from the substrate scopes, the mechanisms and potential applications of some representative methodologies are also included.

Key words: copper catalysis, asymmetric synthesis, chiral organophosphorus compounds, P-chirality

引用此文

李晖, 殷亮. 铜催化的手性膦化合物不对称合成研究进展[J]. 有机化学, doi: 10.6023/cjoc202405002.

Hui Li, Liang Yin. Research Progress on Copper-Catalyzed Asymmetric Synthesis of Chiral Organophosphorus Compounds[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405002.

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参考文献

[1] (a) Mucha, A.; Kafarski, P.; Berlicki, L. J. Med. Chem. 2011, 54, 5955.
(b) Horsman, G. P.; Zechel, D. L. Chem. Rev. 2017, 117, 5704.
(c) Kahler, J. P.; Verhelst, S. H. L. RSC Chem. Biol. 2021, 2, 1285.
(d) Stieger, C. E.; Franz, L.; Körlin, F.; Hackenberger, C. P. R. Angew. Chem., Int. Ed. 2021, 60, 15359.
[2] (a) Chew, R. J.; Leung, P.-H. Chem. Rec. 2016, 16, 141.
(b) Li, Z.; Duan, W. Chin. J. Org. Chem. 2016, 36, 1805 (in Chinese).
(李振, 段伟良, 有机化学, 2016, 36, 1805).
(c) Cain, M. F.; Hughes, R. P.; Glueck, D. S.; Golen, J. A.; Moore, C. E.; Rheingold, A. L. Inorg. Chem. 2010, 49, 7650.
(d) Glueck, D. S. Dalton Trans. 2008, 5276.
(e) Wang, G.; Gibbons, S. K.; Glueck, D. S.; Sibbald, C.; Fleming, J. T.; Higham, L. J.; Rheingold, A. L. Organometallics 2018, 37, 1760.
[3] Gibbons, S. K.; Valleau, C. R.; Peltier, J. L.; Cain, M. F.; Hughes, R. P.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Inorg. Chem. 2019, 58, 8854.
[4] Gallant, S. K.; Tipker, R. M.; Glueck, D. S. Organometallics 2022, 41, 1721.
[5] Chen, Y.-R.; Feng, J.-J.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 595.
[6] Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559.
[7] Chew, R. J.; Lu, Y.; Jia, Y.-X.; Li, B.-B.; Wong, E. H. Y.; Goh, R.; Li, Y.; Huang, Y.; Pullarkat, S. A.; Leung, P.-H. Chem. -Eur. J. 2014, 20, 14514.
[8] Li, Y.-B.; Tian, H.; Yin, L. J. Am. Chem. Soc. 2020, 142, 20098.
[9] Wang, Y.; Wang, Z.-Q.; Yin, L. Synthesis 2023, 55, 2228.
[10] Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
[11] (a) Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.
(b) Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1978, 100, 5491.
(c) Nagel, U. Angew. Chem., Int. Ed. 1984, 23, 435.
(d) Burk, M. J. Acc. Chem. Res. 2000, 33, 363.
[12] Zhang, Y.; Zhang, F.; Chen, L.; Xu, J.; Liu, X.; Feng, X. ACS Catal. 2019, 9, 4834.
[13] Yue, W.-J.; Xiao, J.-Z.; Zhang, S.; Yin, L. Angew. Chem., Int. Ed. 2020, 59, 7057.
[14] (a) Yin, L.; Takada, H.; Lin, S.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2014, 53, 5327.
(b) Ogawa, T.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2012, 51, 8551.
(c) Yanagida, Y.; Yazaki, R.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2011, 50, 7910.
(d) Yazaki, R.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 10275.
[15] Yang, Q.; Zhou, J.; Wang, J. Chem. Sci. 2023, 14, 4413.
[16] (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
(b) Carroll, M. P.; Guiry, P. J. Chem. Soc. Rev. 2014, 43, 819.
(c) Rokade, B. V.; Guiry, P. J. ACS Catal. 2018, 8, 624.
[17] Zhang, Y.; Zhu, S. Acta Chim. Sinica 2023, 81, 777 (in Chinese).
(张艳东, 朱守非, 化学学报, 2023, 81, 777).
[18] Zhang, S.; Jiang, N.; Xiao, J.-Z.; Lin, G.-Q.; Yin, L. Angew. Chem., Int. Ed. 2023, 62, e202218798.
[19] Daniels, B. S.; Hou, X.; Corio, S. A.; Weissman, L. M.; Dong, V. M.; Hirschi, J. S.; Nie, S. Angew. Chem., Int. Ed. 2023, 62, e202306511.
[20] (a) Dian, L.; Marek, I. Chem. Rev. 2018, 118, 8415.
(b) Raiguru, B. P.; Nayak, S.; Mishra, D. R.; Das, T.; Mohapatra, S.; Mishra, N. P. Asian J. Org. Chem. 2020, 9, 1088.
[21] Yu, Y.-N.; Xu, M.-H. Acta Chim. Sin. 2017, 75, 655.
[22] (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
(b) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
(c) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743.
[23] Cai, B.; Cui, Y.; Zhou, J.; Wang, Y.-B.; Yang, L.; Tan, B.; Wang, J. Angew. Chem., Int. Ed. 2023, 62, e202215820.
[24] Zhang, S.; Xiao, J.-Z.; Li, Y.-B.; Shi, C.-Y.; Yin, L. J. Am. Chem. Soc. 2021, 143, 9912.
[25] Beaud, R.; Phipps, R. J.; Gaunt, M. J. J. Am. Chem. Soc. 2016, 138, 13183.
[26] Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776.
[27] (a) Luan, C.; Yang, C.-J.; Liu, L.; Gu, Q.-S.; Liu, X.-Y. Chem Catalysis 2022, 2, 2876.
(b) Moncarz, J. R.; Laritcheva, N. F.; Glueck, D. S. J. Am. Chem. Soc. 2002, 124, 13356.
(c) Korff, C.; Helmchen, G. Chem. Commun. 2004, 530.
(d) Zhang, Y.; He, H.; Wang, Q.; Cai, Q. Tetrahedron Lett. 2016, 57, 5308.
(e) Dai, Q., Li, W., Li, Z., and Zhang, J. J. Am. Chem. Soc. 2019, 141, 20556.
[28] Bhat, V.; Welin, E. R.; Guo, X. L.; Stoltz, B. M. Chem. Rev. 2017, 117, 4528.
[29] Li, Y.; Jin, X.; Liu, P.; Zhang, H.; Yu, X.; Liu, Y.; Liu, B.; Yang, W. Angew. Chem., Int. Ed. 2022, 61, e202117093.
[30] Liu, B.; Liu, P.; Wang, X.; Feng, F.; Wang, Z.; Yang, W. Org. Lett. 2023, 25, 2178.
[31] (a) Kang, J.; Ding, K.; Ren, S.-M.; Su, B. Angew. Chem., Int. Ed. 2023, 62, e202301628.
(b) Kang, J.; Ren, S.; Su, B. Synlett. 2023, 34, DOI: 10.1055/a-2127-1305.
[32] Zhang, X.; Tan, C.-H. Chem 2021, 7, 1451.
[33] (a) Zhou, H.; Li, Z.-L.; Gu, Q.-S.; Liu, X.-Y. ACS Catal. 2021, 11, 7978.
(b) Gu, Q.-S.; Li, Z.-L.; Liu, X.-Y. Acc. Chem. Res. 2020, 53, 170.
(c) Zhang, C.; Li, Z.-L.; Gu, Q.-S.; Liu, X.-Y. Nat. Commun. 2021, 12, 475.
[34] Wang, L-.L.; Zhou, H.; Cao, Y.-X.; Zhang, C.; Ren, Y.-Q.; Li, Z.-L.; Gu, Q.-S.; Liu, X.-Y. Nat. Synth. 2023, 2, 430.
[35] Ye, J.-J.; Nie, S.-Z.; Wang, J.-P.; Wen, J.-H.; Zhang, Y.; Qiu, M.-R.; Zhao, C.-Q. Org. Lett. 2017, 19, 5384.
[36] Li, Y.-B.; Tian, H.; Zhang, S.; Xiao, J.-Z.; Yin, L. Angew. Chem., Int. Ed. 2022, 61, e202117760.

铜催化的手性膦化合物不对称合成研究进展

Research Progress on Copper-Catalyzed Asymmetric Synthesis of Chiral Organophosphorus Compounds

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