SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 6: 1786 - 1792

DOI: https://doi.org/10.6023/cjoc202401010

REVIEWS

Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles

  • Jiasheng Wang ,
  • Zeshu Wang ,
  • Weimin He ,
  • Longwu Ye
Expand
  • a College of Chemistry and Chemical Engineering, Nanhua University, Hengyang, Hunan 421001
    b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
†These authors contributed equally to this work.
* E-mail: ;

Received date: 2024-01-12

  Revised date: 2024-02-23

  Online published: 2024-03-13

Supported by

National Natural Science Foundation of China(22125108); Science and Technology Innovation Program of Hunan Province(2023RC4004)

Fold

Abstract

Hydroamination of o-alkynylanilines is an important approach for the synthesis of indoles. On this basis, o-alkynylanilines bearing substituents with certain steric hindrance could undergo chiral transition-metal catalyzed or organocatalytic atroposelective 5-endo-dig cyclolization for the synthesis of axially chiral indoles. Classified by the types of chiral axes in the products of enantioselective hydroamination, the catalytic enantioselective methods for the preparation of axially chiral indoles containing C—N, C—C and N—N chiral axes are systematically introduced.

Key words： asymmetric catalysis; hydroamination reaction; axially chiral indole; alkyne

Cite this article

Jiasheng Wang , Zeshu Wang , Weimin He , Longwu Ye . Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1786 -1792 . DOI: 10.6023/cjoc202401010

References

[1]
For selected reviews on axially chiral chemistry, see: (a) Zhang, H.-H.; Li, T.-Z.; Liu, S.-J.; Shi, F. Angew. Chem., Int. Ed. 2023, e202311053.
[1]
(b) Song, T.; Li, R.; Huang, L.; Jia, S.; Mei, G. Chin. J. Org. Chem. 2023, 43, 1977. (in Chinese)
[1]
(宋亭谕, 李冉, 黄利华, 贾世琨, 梅光建, 有机化学, 2023, 43, 1977.)
[1]
(c) Chen, Y.-B.; Yang, Y.-N.; Huo, X.-Z.; Ye, L.-W.; Zhou, B. Sci. China: Chem. 2023, 66, 2480.
[1]
(d) Cheng, J. K.; Xiang, S.-H.; Tan, B. Acc. Chem. Res. 2022, 55, 2920.
[1]
(e) Zhang, Z.-X.; Zhai, T.-Y.; Ye, L.-W. Chem. Catal. 2021, 1, 1378.
[1]
(f) Kitagawa, O. Acc. Chem. Res. 2021, 54, 719.
[1]
(g) Wang, Y.-B.; Tan, B. Acc. Chem. Res. 2018, 51, 534.
[2]
For selected reviews on axially chiral indole chemistry, see: (a) Cheng, J. K.; Tan, B. Chem. Rec. 2023, e202300147.
[2]
(b) Zhang, H.-H.; Shi, F. Acc. Chem. Res. 2022, 55, 2562.
[2]
(c) Zhang, Y.-C.; Jiang, F.; Shi, F. Acc. Chem. Res. 2020, 53, 425.
[2]
(d) Li, T.-Z.; Liu, S.-J.; Tan, W.; Shi, F. Chem.-Eur. J. 2020, 26, 15779.
[3]
For selected examples on axially chiral natural products and bioactive molecules, see: (a) Chen, Z.-H.; Li, T.-Z.; Wang, N.-Y.; Ma, X.-F.; Ni, S.-F.; Zhang, Y.-C.; Shi, F. Angew. Chem., Int. Ed. 2023, 62, e202300419.
[3]
(b) Chen, K.-W.; Chen, Z.-H.; Yang, S.; Wu, S.-F.; Zhang, Y.-C.; Shi, F. Angew. Chem., Int. Ed. 2022, 61, e202116829.
[3]
(c) Zhang, Q.; Ma?ndi, A.; Li, S.; Chen, Y.; Zhang, W.; Tian, X.; Zhang, H.; Li, H.; Zhang, W.; Zhang, S.; Ju, J.; Kurta?n, T.; Zhang, C. Eur. J. Org. Chem. 2012, 2012, 5256.
[3]
(d) Tsuda, M.; Takahashi, Y.; Fromont, J.; Mikami, Y.; Kobayashi, J. J. Nat. Prod. 2005, 68, 1277.
[3]
(e) Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfarth, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703.
[3]
(f) Ito, C.; Wu, T.-S.; Furukawa, H. Chem. Pharm. Bull. 1990, 38, 1143.
[3]
(g) Norton, R. S.; Wells, R. J. J. Am. Chem. Soc. 1982, 104, 3628.
[4]
For selected examples on axially chiral catalysts and ligands, see: (a) Mino, T.; Komatsu, S.; Wakui, K.; Yamada, H.; Saotome, H.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2010, 21, 711.
[4]
(b) Mino, T.; Ishikawa, M.; Nishikawa, K.; Wakui, K.; Sakamoto, M. Tetrahedron: Asymmetry 2013, 24, 499.
[4]
(c) Peng, L.; Li, K.; Xie, C.; Li, S.; Xu, D.; Qin, W.; Yan, H. Angew. Chem., Int. Ed. 2019, 58, 17199.
[4]
(d) Sheng, F.-T.; Yang, S.; Wu, S.-F.; Zhang, Y.-C.; Shi, F. Chin. J. Chem. 2022, 40, 2151.
[4]
(e) Wu, P.; Yu, L.; Gao, C.-H.; Cheng, Q.; Deng, S.; Jiao, Y.; Tan, W.; Shi, F. Fundam. Res. 2023, 3, 237.
[4]
(f) Wang, J.-Y.; Gao, C.-H.; Ma, C.; Wu, X.-Y.; Ni, S.-F.; Tan, W.; Shi, F. Angew. Chem., Int. Ed. 2024, 63, e202316454.
[5]
For a selected review, see: Krüger, K.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2153.
[6]
Ototake, N.; Morimoto, Y.; Mokuya, A.; Fukaya, H.; Shida, Y.; Kitagawa, O. Chem.-Eur. J. 2010, 16, 6752.
[7]
(a) He, Y.-P.; Wu, H.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2020, 59, 2105.
[7]
(b) Li, X.; Zhao, L.; Qi, Z.; Li, X. Org. Lett. 2021, 23, 5901.
[7]
(c) Yang, W.-C.; Chen, X.-B.; Song, K.-L.; Wu, B.; Gan, W.-E.; Zheng, Z.-J.; Cao, J.; Xu, L.-W. Org. Lett. 2021, 23, 1309.
[7]
(d) Wang, C.-S.; Wei, L.; Fu, C.; Wang, X.-H.; Wang, C.-J. Org. Lett. 2021, 23, 7401.
[8]
For recent selected reviews on ynamide reactivity, see: (a) Hu, Y.-C.; Zhao, Y.; Wan, B.; Chen, Q.-A. Chem. Soc. Rev. 2021, 50, 2582.
[8]
(b) Chen, Y.-B.; Qian, P.-C.; Ye, L.-W. Chem. Soc. Rev. 2020, 49, 8897.
[8]
(c) Hong, F.-L.; Ye, L.-W. Acc. Chem. Res. 2020, 53, 2003.
[8]
(d) Zhou, B.; Tan, T.-D.; Zhu, X.-Q.; Shang, M.; Ye, L.-W. ACS Catal. 2019, 9, 6393.
[8]
(e) Evano, G.; Theunissen, C.; Lecomte, M. Aldrichim. Acta 2015, 48, 59.
[8]
(f) Wang, X.-N.; Yeom, H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2014, 47, 560.
[9]
For selected reviews on asymmetric synthesis based on ynamides, see: (a) Luo, J.; Chen, G.-S.; Chen, S.-J.; Yu, J.-S.; Li, Z.-D.; Liu, Y.-L. ACS Catal. 2020, 10, 13978.
[9]
(b) Lynch, C. C.; Sripada, A.; Wolf, C. Chem. Soc. Rev. 2020, 49, 8543.
[10]
(a) Zhou, B.; Zhang, Y.-Q.; Zhang, K.; Yang, M.-Y.; Chen, Y.-B.; Li, Y.; Peng, Q.; Zhu, S.-F.; Zhou, Q.-L.; Ye, L.-W. Nat. Commun. 2019, 10, 3234.
[10]
(b) Chen, P.-F.; Zhou, B.; Wu, P.; Wang, B.; Ye, L.-W. Angew. Chem., Int. Ed. 2021, 60, 27164.
[10]
(c) Zhang, Y.-Q.; Chen, Y.-B.; Liu, J.-R.; Wu, S.-Q.; Fan, X.-Y.; Zhang, Z.-X.; Hong, X.; Ye, L.-W. Nat. Chem. 2021, 13, 1093.
[10]
(d) Li, H.-H.; Zhang, Y.-P.; Zhai, T.-Y.; Liu, B.-Y.; Shi, C.-Y.; Zhou, J.-M.; Ye, L.-W. Org. Chem. Front. 2022, 9, 3709.
[10]
(e) Xu, Y.; Qian, G.-L.; Cui, D.-Q.; Qian, P.-C.; Zhao, C.-Y.; Hong, X.; Zhou, B.; Ye, L.-W. ACS Catal. 2023, 13, 8803.
[10]
(f) Li, H.-H.; Meng, Y.-N.; Chen, C.-M.; Wang, Y.-Q.; Zhang, Z.-X.; Xu, Z.; Zhou, B.; Ye, L.-W. Sci. China: Chem. 2023, 66, 1467.
[10]
(g) Zhang, Z.-X.; Wang, X.; Jiang, J.-T.; Chen, J.; Zhu, X.-Q.; Ye, L.-W. Chin. Chem. Lett. 2023, 34, 107647.
[10]
(h) Fan, X.-Y.; Li, J.-C.; Zhou, J.-J.; Zhou, B.; Ye, L.-W. Green Chem. 2023, 25, 10638.
[10]
(i) Cui, D.-Q.; Wang, Y.-Q.; Zhou, B.; Ye, L.-W. Org. Lett. 2023, 25, 9130.
[11]
Wang, Z.-S.; Zhu, L.-J.; Li, C.-T.; Liu, B.-Y.; Hong, X.; Ye, L.-W. Angew. Chem., Int. Ed. 2022, 61, e202201436.
[12]
Xu, D.; Huang, S.; Hu, F.; Peng, L.; Jia, S.; Mao, H.; Gong, X.; Li, F.; Qin, W.; Yan, H. CCS Chem. 2022, 4, 2686.
[13]
Yao, C.-Z.; Xie, Z.-K.; Wang, J.-Y.; Zhang, J.-Y.; Zhao, Z.-Y.; Li, Q.; Yu, J. J. Org. Chem. 2023, 88, 6146.
[14]
Yu, L.; Liu, J.; Xiang, S.; Lu, T.; Ma, P.; Zhao, Q. Org. Lett. 2023, 25, 522.
[15]
Hutskalova, V.; Sparr, C. Synthesis 2023, 55, 1770.
[16]
Wang, C.-S.; Xiong, Q.; Xu, H.; Yang, H.-R.; Dang, Y.; Dong, X.-Q.; Wang, C.-J. Chem. Sci. 2023, 14, 12091.
Options
Outlines

/

〈 〉