SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 8: 2864 - 2877

DOI: https://doi.org/10.6023/cjoc202302017

Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles

  • Yi Wang ,
  • Jian Zhang ,
  • Yangzi Liu ,
  • Xiaoyan Luo ,
  • Weiping Deng
Expand
  • a School of Pharmacy, East China University of Science and Technology, Shanghai 200237
    b College of Chemistry, Zhejiang Normal University, Jinhua 321004
*E-mail: ;

Received date: 2023-02-25

  Revised date: 2023-04-04

  Online published: 2023-04-23

Supported by

The National Key Research and Development Program of China(2021YFA0804900); The National Natural Science Foundation of China(21971062); The National Natural Science Foundation of China(22171082); The Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism

Fold

Abstract

A Pd-catalyzed decarboxylation strategy for the efficient synthesis of cyclohepta[b]indoles in good yields with good to excellent enantioselectivities and moderate diastereoselectivities is reported. In this procedure, viny indoloxazolidones were activated by Pd catalyst to generate zwitterionic intermediates in situ, which were then trapped by the electro-deficient diene species via the asymmetric [3＋4] cycloaddition process.

Key words： decarboxylation; cyclohepta[b]indoles; asymmetric; cycloadditions

Cite this article

Yi Wang , Jian Zhang , Yangzi Liu , Xiaoyan Luo , Weiping Deng . Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2864 -2877 . DOI: 10.6023/cjoc202302017

References

[1]
(a) Guo, W.; Gomez, J. E.; Cristofol, A.; Xie, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2018, 57, 13735.
[1]
(b) Zuo, L.; Liu, T.; Chang, X.; Guo, W. Molecules 2019, 24, 3930.
[1]
(c) Trost, B. M.; Jiao, Z.; Liu, Y.; Ming, C.; J. Hung, C.-I. J. Am. Chem. Soc. 2020, 142, 18628.
[1]
(d) Fairuz Binte Sheikh Ismail, S. N.; Yang, B.; Zhao, Y. Org. Lett. 2021, 23, 2884.
[1]
(e) Yan, B.; Guo, W. Synthesis 2022, 54, 1964.
[1]
(f) Yuan, S.-P.; Bao, Q.; Sun, T.-J.; Zhao, J.-Q.; Wang, Z.-H.; You, Y.; Zhang, Y.-P.; Zhou, M.-Q.; Yuan, W.-C. Org. Lett. 2022, 24, 8348.
[1]
(g) Dou, P.-H.; Yuan, S.-P.; Chen, Y.; Zhao, J.-Q.; Wang, Z.-H.; You, Y.; Zhang, Y.-P.; Zhou, M.-Q.; Yuan, W.-C. J. Org. Chem. 2022, 87, 6025.
[1]
(h) Lu, X.; Xiao, X.; Wan, C.; Wang, Z.; Liu, J. Acta Chim. Sin. 2021, 79, 751.
[1]
(i) Xu, Z.; Malik, A. U.; Shu, M.; Cui, Y. Chin. J. Chem. 2021, 39, 2774.
[1]
(j) Sun, Y.-L.; Tan, F.-F.; Hu, R.-G.; Hu, C.-H.; Li, Y. Chin. J. Chem. 2022, 40, 1903.
[2]
Tian, F.; Yang, W.-L.; Ni, T.; Zhang, J.; Deng, W.-P. Sci. China Chem. 2021, 64, 34.
[3]
Zhao, Z.; Yang, X.-X.; Ran, G.-Y.; Ouyang, Q.; Du, W.; Chen, Y.-C. Org. Lett. 2021, 23, 4791.
[4]
Hang, Q.-Q.; Liu, S.-J.; Yu, L.; Sun, T.-T.; Zhang, Y.-C.; Mei, G.-J.; Shi, F. Chin. J. Chem. 2020, 38, 1612.
[5]
(a) Joseph, B.; Alagille, D.; Merour, J. Y.; Leonce, S. Chem. Pharm. Bull. 2000, 48, 1872.
[5]
(b) Kamata, K.; Suetsugu, T.; Yamamoto, Y.; Hayashi, M.; Komiyama, K.; Ishibashi, M. J. Nat. Prod. 2006, 69, 1252.
[5]
(c) Cao, P.; Liang, Y.; Gao, X.; Li, X.-M.; Song, Z.-Q.; Liang, G. Molecules 2012, 17, 13631.
[6]
(a) Napper, A. D.; Hixon, J.; McDonagh, T.; Keavey, K.; Pons, J. F.; Barker, J.; Yau, W. T.; Amouzegh, P.; Flegg, A.; Hamelin, E.; Thomas, R. J.; Kates, M.; Jones, S.; Navia, M. A.; Saunders, J. O.; DiStefano, P. S.; Curtis, R. J. Med. Chem. 2005, 48, 8045.
[6]
(b) Barf, T.; Lehmann, F.; Hammer, K.; Haile, S.; Axen, E.; Medina, C.; Uppenberg, J.; Svensson, S.; Rondahl, L.; Lundb?ck, T. Med. Chem. Lett. 2009, 19, 1745.
[6]
(c) Yamuna, E.; Kumar, R. A.; Zeller, M.; Prasad, K. J. R. Eur. J. Med. Chem. 2012, 47, 228.
[6]
(d) Liu, B.-Y.; Zhang, C.; Zeng, K.-W.; Li, J.; Guo, X.-Y.; Zhao, M.-B.; Tu, P.-F.; Jiang, Y. Org. Lett. 2015, 17, 4380.
[7]
Gierok, J.; Benedix, L.; Hiersemann, M. Eur. J. Org. Chem. 2021, 26, 3748.
[8]
(a) Hamada, N.; Yoshida, Y.; Oishi, S.; Ohno, H. Org. Lett. 2017, 19, 3875.
[8]
(b) Cheng, B.; Volpin, G.; Morstein, J.; Trauner, D. Org. Lett. 2018, 20, 4358.
[8]
(c) Takeda, T.; Harada, S.; Okabe, A.; Nishida, A. J. Org. Chem. 2018, 83, 11541.
[8]
(d) Wang, Z.; Addepalli, Y.; He, Y. Org. Lett. 2018, 20, 644.
[8]
(e) Tymann, D.; Tymann, D. C.; Bednarzick, U.; Iovkova-Berends, L.; Rehbein, J.; Hiersemann, M. Angew. Chem., Int. Ed. 2018, 57, 15553.
[8]
(f) Tymann, D.; Bednarzick, U.; Iovkova-Berends, L.; Hiersemann, M. Org. Lett. 2018, 20, 4072.
[8]
(g) Kaufmann, J.; J?ckel, E.; Haak, E. Angew. Chem., Int. Ed. 2018, 57, 5908.
[8]
(h) Jadhav, A. S.; Pankhade, Y. A.; Anand, R. V. J. Org. Chem. 2018, 83, 8615.
[8]
(i) Zeng, Q.; Dong, K.; Huang, J.; Qiu, L.; Xu, X. Org. Biomol. Chem. 2019, 17, 2326.
[8]
(j) Parker, A. N.; Martin, M. C.; Shenje, R.; France, S. Org. Lett. 2019, 21, 7268.
[8]
(k) Yuan, Y.; Guo, X.; Zhang, X.; Li, B.; Huang, Q. Org. Chem. Front. 2020, 7, 3146.
[8]
(l) Tymann, D. C.; Benedix, L.; Iovkova, L.; Pallach, R.; Henke, S.; Tymann, D.; Hiersemann, M. Chem.-Eur. J. 2020, 26, 11974.
[8]
(m) Mu, X.-P.; Li, Y.-H.; Zheng, N.; Long, J.-Y.; Chen, S.-J.; Liu, B.-Y.; Zhao, C.-B.; Yang, Z. Angew. Chem., Int. Ed. 2021, 60, 11211.
[8]
(n) Dhawa, U.; Connon, R.; Oliveira, J. C. A.; Steinbock, R.; Ackermann, L. Org. Lett. 2021, 23, 2760.
[9]
(a) Trost, B. M.; Zuo, Z.; Schultz, J. E. Chem.-Eur. J. 2020, 26, 15354.
[9]
(b) Zhao, C.; Khan, L.; Zhang, Y.-J. Chem. Commun. 2020, 56, 12431.
[9]
(c) Du, J.; Hua, Y.-D.; Jiang, Y.-J.; Huang, S.; Chen, D.; Ding, C.-H.; Hou, X.-L. Org. Lett. 2020, 22, 5375.
[9]
(d) Mao, B.; Liu, H.; Yan, Z.; Xu, Y.; Xu, J.; Wang, W.; Wu, Y.; Guo, H. Angew. Chem., Int. Ed. 2020, 59, 11316.
[9]
(e) Guo, J.-M.; Fan, X.-Z.; Wu, H.-H.; Tang, Z.; Bi, X.-F.; Zhang, H.; Cai, L.-Y.; Zhao, H.-W.; Zhong, Q.-D. J. Org. Chem. 2021, 86, 1712.
[9]
(f) Gao, Y.; Zhang, X.; Zhang, X.; Miao, Z. Org. Lett. 2021, 23, 2415.
[9]
(g) García-Vázquez, V.; Hoteite, L.; Lakeland, C. P.; Watson, D. W.; Harrity, J. P. A. Org. Lett. 2021, 23, 2811.
[9]
(h) Zuo, L.; Yang, Y.; Guo, W. Org. Lett. 2021, 23, 2013.
[9]
(i) Yang, G.; Ke, Y.-M.; Zhao, Y. Angew. Chem., Int. Ed. 2021, 60, 12775.
[9]
(j) Peng, Y.; Huo, X.; Luo, Y.; Wu, L. Angew. Chem., Int. Ed. 2021, 60, 24941.
[9]
(k) Wang, D.; Sun, J.; Yan, C.-G. Green Synth. Catal. 2022, 3, 53.
[9]
(l) You, Y.; Li, Q.; Zhang, Y.-P.; Zhao, J.-Q. Wang, Z.-H.; Yuan, W.-C. ChemCatChem 2022, 14, e202101887.
[9]
(m) Xu, B.; Zhang, Z.-M.; Han, J.; Gu, G.; Zhang, J. Chin. J. Chem. 2022, 40, 1407.
[9]
(n) Zhu, M.; Zhang, X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2022, 55, 2510.
[9]
(o) Zhang, W.; Zhang, P.-C.; Li, Y.-L.; Wu, H.-H.; Zhang, J. J. Am. Chem. Soc. 2022, 144, 19627.
[9]
(p) Zhang, M.-M.; Qu, B.-L.; Shi, B.; Xiao, W.-J.; Lu, L.-Q. Chem. Soc. Rev. 2022, 51, 4146.
[9]
(q) Wang, B.-C.; Wei, Y.; Xiong, F.-Y.; Qu, B.-L.; Xiao, W.-J.; Lu, L.-Q. Sci. China. Chem. 2022, 65, 2437.
[9]
(r) Zhang, J.; Chen, Y.; Wang, Q.; Shen, J.; Liu, Y.-Z.; Deng, W.-P. Chin. J. Org. Chem. 2022, 42, 3051.
[9]
(s) Hui, M.; Li, B.; Gong, B.; Yao, H.; Lin, A. Chem. Commun. 2022, 58, 2850.
[10]
(a) Li, Y.; Zhu, C.-Z.; Zhang, J. Eur. J. Org. Chem. 2017, 6609.
[10]
(b) Xu, G.; Chen, L.; Sun, J. Org. Lett. 2018, 20, 3408.
[10]
(c) Pirovano, V.; Brambilla, E.; Moretti, A.; Rizzato, S.; Abbiati, G.; Nava, D.; Rossi, E. J. Org. Chem. 2020, 85, 3265.
[10]
(d) Yang, W.-L.; Li, W.; Yang, Z.-T.; Deng, W.-P. Org. Lett. 2020, 22, 4026.
[11]
(a) Zhang, H.-H.; Zhu, Z.-Q.; Fan, T.; Liang, J.; Shi, F. Adv. Synth. Catal. 2016, 358, 1259.
[11]
(b) Liu, J.; Wang, L.; Wang, X.; Xu, L.; Hao, Z.; Xiao, J. Org. Biomol. Chem. 2016, 14, 11510.
[11]
(c) Gelis, C.; Levitre, G.; Merad, J.; Retailleau, P.; Neuville, L.; Masson, G. Angew. Chem., Int. Ed. 2018, 57, 12121.
[11]
(d) Cheng, Q.; Xie, J.-H.; Weng, Y.-C.; You, S.-L. Angew. Chem., Int. Ed. 2019, 58, 5739.
[12]
(a) Nguyen, T. V.; Hartmann, J. M.; Enders, D. Synthesis 2013, 45, 845.
[12]
(b) Ylijoki, K. E. O.; Stryker, J. M. Chem. Rev. 2013, 113, 2244.
[12]
(c) Yin, Z.; He, Y.; Chiu, P. Chem. Soc. Rev. 2018, 47, 8881.
[12]
(d) Pellissier, H. Adv. Synth. Catal. 2018, 360, 1551.
[12]
(e) Gao, K.; Zhang, Y.-G.; Wang, Z.; Ding, H. Chem. Commun. 2019, 55, 1859.
[13]
(a) Liu, Y.-Z.; Wang, Z.; Huang, Z.; Zheng, X.; Yang, W.-L.; Deng, W.-P. Angew. Chem. Int. Ed. 2020, 59, 1238.
[13]
(b) Zheng, X.; Sun, H.; Yang, W.-L.; Deng, W.-P. Sci. China. Chem. 2020, 63, 911.
[13]
(c) Yang, W.-L.; Huang, Z.; Liu, Y.-Z.; Yu, X.; Deng, W.-P. Chin. J. Chem. 2020, 38, 1571.
[13]
(d) Yang, W.-L.; Li, W.; Yang, Z.-T.; Deng, W.-P. Org. Lett. 2020, 22, 4026.
[13]
(e) Yang, W.-L.; Ni, T.; Deng, W.-P. Org. Lett. 2021, 23, 588.
[13]
(f) Liu, Y.-Z.; Wang, Z.; Huang, Z.; Yang, W.-L.; Deng, W.-P. Org. Lett. 2021, 23, 948.
[13]
(g) Yang, W.-L.; Shen, J.-H.; Zhao, Z.-H.; Wang, Z.; Deng, W.-P. Org. Chem. Front. 2022, 9, 4685.
[13]
(h) Tan, W.; Zhang, J.-Y.; Gao, C.-H.; Shi, F. Sci. China. Chem. 2023, 66, DOI: 10.1007/s11426-022-1471-2.
[14]
Gu, B.-Q.; Yang, W.-L.; Wu, S.-X.; Wang, Y.-B.; Deng, W.-P. Org. Chem. Front. 2018, 5, 3430.
Options
Outlines

/

〈 〉