综述与进展

金和手性磷酸共催化的不对称合成研究进展

  • 朱晓宇 ,
  • 杨诗林 ,
  • 罗宜铭 ,
  • 李文泽
展开
  • 沈阳化工大学 辽宁省稀土化学及应用重点实验室 沈阳 110142

收稿日期: 2024-07-18

  修回日期: 2024-09-05

  网络出版日期: 2024-10-18

基金资助

辽宁省教育厅基金(LJKMZ20220795)

Advances of Asymmetric Synthesis Combining of Gold and Chiral Phosphoric Acid Catalysts

  • Xiaoyu Zhu ,
  • Shilin Yang ,
  • Yiming Luo ,
  • Wenze Li
Expand
  • Liaoning Key Laboratory of Rare Earth Chemistry and Application, Shenyang University of Chemical Technology, Shenyang 110142

Received date: 2024-07-18

  Revised date: 2024-09-05

  Online published: 2024-10-18

Supported by

Liaoning Provincial Department of Education Fund(LJKMZ20220795)

摘要

均相金催化在近年来发展迅速并取得了极大进展, 然而金(I)配合物的线性结构以及Au(III)有机配合物的不稳定性限制了其在很多不对称催化反应中的应用. 将金催化与有机催化结合起来, 能够实现优势互补, 大大拓展了不对称金催化的应用范围. 手性磷酸是一种结构独特的双功能有机催化剂, 其与过渡金属联合催化, 发展了很多单一催化剂难以实现的新反应. 综述了金和手性磷酸共催化进行不对称合成的研究进展, 从抗衡阴离子导向催化、协同催化和接力催化等三个方面进行了总结探讨, 并对其发展前景进行了展望.

本文引用格式

朱晓宇 , 杨诗林 , 罗宜铭 , 李文泽 . 金和手性磷酸共催化的不对称合成研究进展[J]. 有机化学, 2025 , 45(4) : 1178 -1193 . DOI: 10.6023/cjoc202407033

Abstract

Homogeneous gold catalysis has developed rapidly and made great progress in recent years, however, the linear structure of Au(I) complexes and the instability of Au(III) organic complexes limit their application in many asymmetric catalytic reactions. Combining gold with organic small molecules as cocatalysts may promote complementary advantages and greatly expand the application scope of asymmetric gold catalysis. Chiral phosphoric acid is a kind of bifunctional organic catalyst with novel structure. Combining chiral phosphoric acids with transition metals can catalyze many new reactions that are difficult to realize with a single catalyst. The asymmetric reactions catalyzed by gold and chiral phosphoric acid are summarized from three aspects, including counter anion directed catalysis, cooperative catalysis and relay catalysis, as well as the latest research progress and development prospects are also discussed.

参考文献

[1]
Hashmi, A. S. K.; Hutching, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896.
[2]
Bond, G. C.; Sermon, P. A.; Webb, G.; Buchanan, D. A.; Wells, P. B. J. Chem. Soc., Chem. Commun. 1973, 444.
[3]
Hutchings, G. J. J. Catal. 1985, 96, 292.
[4]
Haruta, M.; Yamada, N.; Kobayashi, T.; Iijima, S. J. Catal. 1989, 115, 301.
[5]
Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
[6]
(a) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297.
[6]
(b) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
[6]
(c) Fukuda, Y.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2013.
[7]
(a) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415.
[7]
(b) Hashimi, A. S. K. Gold Bull. 2004, 37, 51.
[8]
(a) Hashimi, A. S. K. Chem. Rev. 2007, 107, 3180.
[8]
(b) Jimenz-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
[8]
(c) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
[8]
(d) Arcadi, A. Chem. Rev. 2008, 108, 3266.
[8]
(e) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
[9]
Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
[10]
Mu?oz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
[11]
Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
[12]
(a) Widenhoefer, R. A. Chem. Eur. J. 2008, 14, 5382.
[12]
(b) Sengupta, S.; Shi, X. ChemCatChem 2010, 2, 609.
[12]
(c) Wang, Y.-M.; Lackner, A. D.; Toste, F. D. Acc. Chem. Res. 2014, 47, 889.
[12]
(d) Zi, W.; Dean Toste, F. Chem. Soc. Rev. 2016, 45, 4567.
[12]
(e) Rodriguez, J.; Bourissou, D. Angew. Chem., Int. Ed. 2018, 57, 386.
[13]
(a) Chen, G.-S.; Deng, Y.-J.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567.
[13]
(b) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329.
[14]
(a) Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2010, 2999.
[14]
(b) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337.
[14]
(c) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365.
[15]
Han, Z.-Y.; Wang, C.; Gong, L.-Z. In Science of Synthesis: Asymmetric Organocatalysis, Ed.: Maruoka, K., Vol. 2, Georg Thieme Verlag, Stuttgart, 2012, p. 697.
[16]
Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nat. Chem. 2012, 4, 603.
[17]
(a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
[17]
(b) Terada, M. Synthesis 2010, 1929.
[17]
(c) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156.
[17]
(d) Gao, Y.-J.; Yang, L.-H.; Song, S.-J.; Ma, J.-J.; Tang, R.-X.; Bian, R.-H.; Liu, H.-Y.; W, Q.-H.; Wang, C. Chin. J. Org. Chem. 2008, 28, 8 (in Chinese).
[17]
(高勇军, 杨丽华, 宋双居, 马晶军, 唐然肖, 边瑞环, 刘海燕, 吴秋华, 王春, 有机化学, 2008, 28, 8.)
[17]
(e) Su, Y.-J.; Shi, F.-Q. Chin. J. Org. Chem. 2010, 30, 486 (in Chinese).
[17]
(苏亚军, 史福强, 有机化学, 2010, 30, 486.)
[18]
(a) Shao, Z.-H.; Zhang, H.-B. Chem. Soc. Rev. 2009, 38, 2745.
[18]
(b) Wu, X.; Li, M.-L.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 1091 (in Chinese).
[18]
(吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.)
[18]
(c) Sun, Z.; H, J.-M.; Q, M.-N.; L, K.-S. Chin. J. Org. Chem. 2015, 35, 1250 (in Chinese).
[18]
(孙哲, 何金梅, 屈孟男, 李侃社, 有机化学, 2015, 35, 1250.)
[18]
(d) Cui, X.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. Chin. J. Org. Chem. 2022, 42, 3033 (in Chinese).
[18]
(崔效源, 周锋, 吴海虹, 周剑, 有机化学, 2022, 42, 3033.)
[18]
(e) Xiang, X.; He, Z.-L.; Dong, X.-Q. Chin. J. Org. Chem. 2023, 43, 791 (in Chinese)
[18]
(向勋, 何照林, 董秀琴, 有机化学, 2023, 43, 791).
[19]
Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496.
[20]
(a) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
[20]
(b) Zhong, C.; Shi, X.-D. Eur. J. Org. Chem. 2010, 16, 2999.
[21]
Aikawa, K.; Kojima, M.; Mikami, K. Adv. Synth. Catal. 2010, 352, 3131.
[22]
Mourad, A. K.; Leutzow, J.; Czekelius, C. Angew. Chem., Int. Ed. 2012, 51, 11149.
[23]
Tu, X.-F.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 1.
[24]
Du, Y.-L.; Hu, Y.; Zhu, Y.-F.; Tu, X.-F.; Han, Z.-Y.; Gong, L.-Z. J. Org. Chem. 2015, 80, 4754.
[25]
Zhang, Z.-H.; Smal, V.; Retailleau, P.; Voituriez, A.; Frison, G.; Marinetti, A.; Guinchard, X. J. Am. Chem. Soc. 2020, 142, 3797.
[26]
Yu, Y.-L.; Zhang, Z.-H.; Voituriez, A.; Rabasso, N.; Frison, G.; Marinetti, A.; Guinchard, X. Chem. Commun. 2021, 57, 10779.
[27]
Zhang, Z.-H.; Sabat, N.; Frison, G.; Marinetti, A.; Guinchard, X. ACS Catal. 2022, 12, 4046.
[28]
Patil, N. T.; Raut, V. S.; Tella, R. B. Chem. Commun. 2013, 49, 570.
[29]
Wei, H.-L.; Bao, M.; Dong, K.-Y.; Qiu, L.-H.; Wu, B.; Hu, W.-H.; Xu, X.-F. Angew. Chem., Int. Ed. 2018, 57, 17200.
[30]
Zhou, S.; Li, Y.-W.; Liu, X.-R.; Hu, W.-H.; Ke, Z.-F.; Xu, X.-F. J. Am. Chem. Soc. 2021, 143, 14703.
[31]
Liu, X.-S.; Tang, Z.-Q.; Zhang, Z.-K.; Zhao, L.; Liu, L. Angew. Chem., Int. Ed. 2022, 61, e202208874.
[32]
Chen, K.-W.; Zhou, S.; Li, C.; Dong, S.-L.; Hong, K.-M.; Xu, X.-F. J. Am. Chem. Soc. 2024, 146, 19261.
[33]
Han, Z.-Y.; Xiao, H.; Chen, X.-H. Gong, L.-Z. J. Am. Chem. Soc. 2003, 131, 9182.
[34]
Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204.
[35]
Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. L.; Trevitt, G.; Dixone, D. J. J. Am. Chem. Soc. 2009, 131, 10796.
[36]
Wang, C.; Han, Z.-Y.; Luo, H.-W.; Gong, L.-Z. Org, Lett. 2010, 12, 2266.
[37]
Han, Z.-Y.; Guo, R.; Wang, P.-S.; Chen, D.-F.; Xiao, H.; Gong, L.-Z. Tetrahedron Lett. 2011, 52, 5963.
[38]
Han, Z.-Y.; Chen, D.-F.; Wang, Y.-Y.; Guo, R.; Wang, P.-S.; Wang, C.; Gong, L.-Z. J. Am. Chem. Soc. 2012, 134, 6532.
[39]
Fleischer, S.; Werkmeister, S.; Zhou, S.-L.; Junge, K.; Beller, M. Chem. Eur. J. 2012, 18, 9005.
[40]
Patil, N. T.; Mutyala, A. K.; Konala, A.; Tella, R. B. Chem. Commun. 2012, 48, 3094.
[41]
Liu, X.-Y.; Xiao, Y.-P.; Siu, F.-M.; Ni, L.-C.; Chen, Y.; Wang, L.; Che, C.-M. Org. Biomol. Chem. 2012, 10, 7208.
[42]
Qian, D.-Y.; Zhang, J.-L. Chem.-Eur. J. 2013, 19, 6984.
[43]
He, Y.-P.; Wu, H.; Chen, D.-F.; Yu, J.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 5232.
[44]
Wu, H.; He, Y.-P.; Gong, L.-Z. Org. Lett. 2013, 15, 460.
[45]
Cala, L.; Mendoza, A.; Fan?ana?s, F. J.; Rodríguez, F. Chem. Commun. 2013, 48, 2715.
[46]
Gregory, A. W.; Jakubec, P.; Turner, P.; Dixon, D. J. Org, Lett. 2013, 15, 4330.
[47]
Calleja, J.; Gonza?lez-Pe?rez, A. B.; de Lera, A. R.; álvarez, R.; Fan?ana?s, F. J.; Rodríguez, F. Chem. Sci. 2014, 5, 996.
[48]
Shinde, V. S.; Mane, M. V.; Vanka, K.; Mallick, A.; Patil, N. T. Chem.-Eur. J. 2014, 20, 1.
[49]
Rexit, A. A.; Mailikezati, M. Tetrahedron Lett. 2015, 56, 2651.
[50]
Zhao, F.; Li, N.; Zhu, Y.-F.; Han, Z.-Y. Org. Lett. 2016, 18, 1506.
[51]
Zhao, F.; Li, N.; Zhang, T.; Han, Z.-Y.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2017, 56, 1.
文章导航

/