基于去对称化策略合成磷中心手性化合物的研究进展
收稿日期: 2024-06-20
修回日期: 2024-09-30
网络出版日期: 2024-10-18
基金资助
国家自然科学基金(21602065); 国家自然科学基金(21931013); 福建省自然科学基金(2022J02009); 河南师范大学化学化工学院开放基金资助项目.
Recent Advances in the Synthesis of P-Stereogenic Compounds via Desymmetrization Strategy
Received date: 2024-06-20
Revised date: 2024-09-30
Online published: 2024-10-18
Supported by
National Natural Science Foundation of China(21602065); National Natural Science Foundation of China(21931013); Natural Science Foundation of Fujian Province(2022J02009); Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University.
林国涛 , 许健 , 宋秋玲 . 基于去对称化策略合成磷中心手性化合物的研究进展[J]. 有机化学, 2024 , 44(12) : 3621 -3638 . DOI: 10.6023/cjoc202406029
Organophosphorus compounds are extensively utilized in the field of medicine, materials, life sciences, and organic synthesis, among which chiral phosphorus compounds are the most widely used. Therefore, the construction of chiral phosphorus centers has always been the hotspot and challenge in organic synthesis. Traditional synthesis methods are mainly focused on chiral resolution and chiral induction strategies. Recently, the construction of chiral phosphorus centers via asymmetric catalysis has been well developed. The recently development of desymmetrization strategies in the construction of phos- phorus centers is summarized, mainly focused on the transformation of C—H, C=C, C≡C bonds and hydroxyl group. What’s more, the deficiencies of current strategies and the trends of future development have also been discussed.
Key words: P-stereogenic center; desymmetrization; C—H bond activation
| [1] | (a) Rodriguez J. B.; Gallo-Rodriguez C. ChemMedChem 2018, 14, 190. |
| [1] | (b) Dutartre M.; Bayardon J.; Jugé S. Chem. Soc. Rev. 2016, 45, 5771. |
| [1] | (c) Mehellou Y.; Rattan H. S.; Balzarini J. J. Med. Chem. 2018, 61, 2211 |
| [2] | (a) Tang W.; Zhang X. Chem. Rev. 2003, 103, 3029. |
| [2] | (b) Fernández-Pérez H.; Etayo P.; Panossian A.; Vidal-Ferran A. Chem. Rev. 2011, 111, 2119. |
| [2] | (c) van Leeuwen P. W. N.; Kamer M. P. C. J.; Claver C.; Pàmies O.; Diéguez M. Chem. Rev. 2011, 111, 2077. |
| [2] | ((d) Zhang Y.; Zhu S. Acta Chim. Sinica 2023, 81, 777 (in Chinese). |
| [2] | (张艳东, 朱守非, 化学学报, 2023, 81, 777.) |
| [3] | (a) Ray A. S.; Fordyce M. W.; Hitchcock M. J. M. Antiviral Res. 2016, 125, 63. |
| [3] | (b) Wang Y.; Zhang D.; Du G.; Du R.; Zhao J.; Jin Y.; Fu S.; Gao L.; Cheng Z.; Lu Q.; Hu Y.; Luo G.; Wang K.; Lu Y.; Li H.; Wang S.; Ruan S.; Yang C.; Mei C.; Wang Y.; Ding D.; Wu F.; Tang X.; Ye X.; Ye Y.; Liu B.; Yang J.; Yin W.; Wang A.; Fan G.; Zhou F.; Liu Z.; Gu X.; Xu J.; Shang L.; Zhang Y.; Cao L.; Guo T.; Wan Y.; Qin H.; Jiang Y.; Jaki T.; Hayden F. G.; Horby P. W.; Cao B.; Wang C. Lancet 2020, 395, 1569. |
| [3] | (c) Pilote L.; Abrahamowicz M.; Eisenberg M.; Humphries K.; Behlouli K. H.; Tu J. V. Can. Med. Assoc. J. 2008, 178, 1303. |
| [4] | (a) Dutartre M.; Bayardon J.; Jugé S. Chem. Soc. Rev. 2016, 45, 5771. |
| [4] | (b) Lemouzy S.; Giordano L.; Hérault D.; Buono G. Eur. J. Org. Chem. 2020, 2020, 3351. |
| [4] | (c) Liu J.; Chen H.; Wang M.; He W.; Yan J. Front. Chem. 2023, 11, 1. |
| [5] | (a) Li H.; Yin L. Chin. J. Org. Chem. 2022, 42, 3183 (in Chinese). |
| [5] | (李晖, 殷亮, 有机化学, 2022, 42, 3183.) |
| [5] | (b) Ye X.; Peng L.; Bao X.; Tan C.-H.; Wang H. Green Synth. Catal. 2021, 2, 6. |
| [6] | (a) Muci A. R.; Campos K. R.; Evans D. A. J. Am. Chem. Soc. 1995, 117, 9075. |
| [6] | (b) Genet C.; Canipa S. J.; O’Brien P.; Taylor S. J. Am. Chem. Soc. 2006, 128, 9336. |
| [6] | (c) Granander J.; Secci F.; Canipa S. J.; O’Brien P.; Kelly B. J. Org. Chem. 2011, 76, 4794. |
| [7] | Qian P.-F.; Li J.-Y.; Zhou Y.-B.; Zhou T.; Shi B.-F. SynOpen 2023, 7, 466. |
| [8] | Du Z.; Guan J.; Wu G.; Xu P.; Gao L.; Han F. J. Am. Chem. Soc. 2015, 137, 632. |
| [9] | Qin X.-L.; Li A.; Han F.-S. J. Am. Chem. Soc. 2021, 143, 2994. |
| [10] | Lin Z.; Wang W.; Yan S.; Duan W. Angew. Chem., Int. Ed. 2015, 54, 6265. |
| [11] | Liu L.; Zhang A.; Wang Y.; Zhang F.; Zuo Z.; Zhao W.-X.; Feng C.-L.; Ma W. Org. Lett. 2015, 17, 2046. |
| [12] | Xu G.; Li M.; Wang S.; Tang W. Org. Chem. Front. 2015, 2, 1342. |
| [13] | Li Z.; Lin Z.; Yan C.; Duan W. Organometallics 2019, 38, 3916. |
| [14] | Zhou T.; Fan L.; Chen Z.; Jiang M.; Qian P.; Hu X.; Zhang K.; Shi B. Org. Lett. 2023, 25, 5724. |
| [15] | Wang C.; Zhou T.; Shi B. ACS Catal. 2024, 14, 7213. |
| [16] | Sun Y.; Cramer N. Angew. Chem., Int. Ed. 2016, 56, 364. |
| [17] | Gwon D.; Lee D.; Kim J.; Park S.; Chang S. Chem.-Eur J. 2014, 20, 12421. |
| [18] | Jang Y.; Dieckmann M.; Cramer N. Angew. Chem., Int. Ed. 2017, 56, 15088. |
| [19] | Jang Y.; Wo?niak ?.; Pedroni J.; Cramer N. Angew. Chem., Int. Ed. 2018, 57, 12901. |
| [20] | Zhang C.-W.; Hu X.-Q.; Dai Y.-H.; Yin P.; Wang C.; Duan W.-L. ACS Catal. 2022, 12, 193. |
| [21] | Genov G.; Douthwaite J.; Lahdenper€a A.; Gibson D.; Phipps R. Science 2020, 367, 1246 |
| [22] | Song S.-Y.; Li Y.; Ke Z.; Xu S. ACS Catal. 2021, 11, 13445. |
| [23] | Yao Q.-J.; Chen J.-H.; Song H.; Huang F.-R.; Shi B-F. Angew. Chem., Int. Ed. 2022, 61, e202202892. |
| [24] | Chen J.-H.; Teng M.-Y.; Huang F.-R.; Song H.; Wang Z.-K.; Zhuang H.-L.; Wu Y.-J.; Wu X.; Yao Q.-J.; Shi B.-F. Angew. Chem., Int. Ed. 2022, 61, e202210106. |
| [25] | Zhou G.; Chen J.-H.; Yao Q.-J.; Huang F.-R.; Wang Z.-K.; Shi B.-F. Angew. Chem., Int. Ed. 2023, 62, e202302964. |
| [26] | Münchow T.; Dana S.; Xu Y.; Yuan B.; Ackermann K. Science 2023, 379, 1036. |
| [27] | Xia X.-Y.; Zheng C.-D.; Hang Y.-F.; Guo J.-Y.; Liu T.; Song D.-G.; Chen Z.-W.; Zhong W.-F.; Ling F. Green Chem. 2024, 26, 8323. |
| [28] | Wiktelius D.; Johansson M.; Luthman K.; Kann N. Org. Lett. 2005, 7, 4991. |
| [29] | Huang Z.; Huang X.; Li B.; Mou C.; Yang S.; Song B.; Chi Y. R. J. Am. Chem. Soc. 2016, 138, 7524. |
| [30] | Yang G.; Li Y.; Li X.; Cheng J. Chem. Sci. 2019, 10, 4322. |
| [31] | Chen Y.-G.; Hu Y.; Liu J.-Y.; Xie M.-S.; Guo H.-M. Org. Chem. Front. 2023, 20, 6140. |
| [32] | Qi Z.-C.; Li Y.; Wang J.; Ma L.; Wang G.-W.; Yang S.-D. ACS Catal. 2023, 13, 13301. |
| [33] | Nishida G.; Noguchi K.; Hirano M.; Tanaka K. Angew. Chem., Int. Ed. 2008, 47, 3410. |
| [34] | Zhu R.-Y.; Chen L.; Hu X.-S.; Zhou F.; Zhou J. Chem. Sci. 2020, 11, 97. |
| [35] | Zhang Y.; Zhang F.; Chen L.; Xu J.; Liu X.; Feng X. ACS Catal. 2019, 9, 4834. |
| [36] | Zheng Y.; Guo L.; Zi W. Org. Lett. 2018, 20, 7039. |
| [37] | Harvey J. S.; Malcolmson S. J.; Dunne K. S.; Meek S. J.; Thompson A. L.; Schrock R. R.; Hoveyda A. H.; Gouverneur V. Angew. Chem., Int. Ed. 2009, 48, 762. |
| [38] | Lim K.; Hayashi T. J. Am. Chem. Soc. 2017, 139, 8122. |
| [39] | Wang Z.; Hayashi T. Angew. Chem., Int. Ed. 2018, 57, 1702. |
| [40] | Forbes C.; Jacobsen E. Science 2022, 376, 1230. |
| [41] | Formica M.; Rogova T.; Shi H.; Sahara N.; Ferko B.; Farley A.; Christensen K.; Duarte F.; Yamazaki K.; Dixon D. Nat. Chem. 2023, 15, 714. |
| [42] | Formica M.; Ferko B.; Marsh T.; Davidson T.; Yamazaki K.; Dixon D. Angew. Chem., Int. Ed. 2024, 63, e202400673. |
| [43] | Wang C.; Huang K.; Ye J.; Duan W. J. Am. Chem. Soc. 2021, 143, 5685 |
| [44] | Wang C.; Yang Q.; Dai Y.; Xiong J.; Zheng Y.; Duan W. Angew. Chem., Int. Ed. 2023, e202313112. |
| [45] | Zhang X.-L.; Qi X.; Wu Y.-X.; Liu P.; He Y. Cell Rep. Phys. Sci. 2021, 2, 100594. |
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