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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 10: 3373 - 3381

DOI: https://doi.org/10.6023/cjoc202209002

ARTICLES

Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles

  • Shihu Jia ,
  • Siyuan Chen ,
  • Zeshui Liu ,
  • Honggang Cheng ,
  • Qianghui Zhou
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  • a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
    b Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001
    c The Institute for Advanced Studies, Wuhan University, Wuhan 430072
* Corresponding authors. E-mail: ;
E-mail:

Received date: 2022-09-01

  Revised date: 2022-10-11

  Online published: 2022-10-20

Supported by

National Natural Science Foundation of China(21871213); National Natural Science Foundation of China(22071189); Fundamental Research Funds for Central Universities(2042021kf0214)

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Abstract

A new type of axially chiral phosphine-alkene ligands have been developed via a two-step modular synthesis for Pd-catalyzed asymmetric allylic alkylation of indoles. Under optimized reaction conditions, a series of chiral allylindole products were obtained in generally high yields (up to 95%) and excellent enantioselectivities (up to 96% ee).

Key words： palladium catalysis; phosphine-alkene ligand; indole; allylic alkylation; asymmetric catalysis

Cite this article

Shihu Jia , Siyuan Chen , Zeshui Liu , Honggang Cheng , Qianghui Zhou . Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3373 -3381 . DOI: 10.6023/cjoc202209002

References

[1]
(a) Saxton, J. E. Nat. Prod. Rep. 1997, 14, 559.
[1]
(b) O'Connor, S. E.; Maresh,, J. J. Nat. Prod. Rep. 2006, 23, 532.
[1]
(c) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
[1]
(d) Lancianesi, S.; Palmieri, A.; Petrini, M. Chem. Rev. 2014, 114, 7108.
[2]
(a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.
[2]
(b) Poulsen, T. B.; Jorgensen, K. A. Chem. Rev. 2008, 108, 2903.
[2]
(c) You, S. L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190.
[3]
(a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
[3]
(b) Chen, J.-B.; Jia, Y.-X. Org. Biomol. Chem. 2017, 15, 3550.
[3]
(c) Pritchett, B. P.; Stoltz, B. M. Nat. Prod. Rep. 2018, 35, 559.
[4]
Cheung, H. Y.; Yu, W. Y.; Lam, F. L.; Au-Yeung, T. T.; Zhou, Z.; Chan, T. H.; Chan, A. S. Org. Lett. 2007, 9, 4295.
[5]
Hoshi, T.; Sasaki, K.; Sato, S.; Ishii, Y.; Suzuki, T.; Hagiwara, H. Org. Lett. 2011, 13, 932.
[6]
Cao, Z.; Liu, Y.; Liu, Z.; Feng, X.; Zhuang, M.; Du, H. Org. Lett. 2011, 13, 2164.
[7]
Liu, Z.; Cao, Z.; Du, H. Org. Biomol. Chem. 2011, 9, 5369.
[8]
Mino, T.; Ishikawa, M.; Nishikawa, K.; Wakui, K.; Sakamoto, M. Tetrahedron: Asymmetry 2013, 24, 499.
[9]
Feng, B.; Pu, X.-Y.; Liu, Z.-C.; Xiao, W.-J.; Chen, J.-R. Org. Chem. Front. 2016, 3, 1246.
[10]
Qiu, Z.; Sun, R.; Yang, K.; Teng, D. Molecules 2019, 24, 1575.
[11]
(a) Xu, J.-X.; Ye, F.; Bai, X.-F.; Zhang, J.; Xu, Z.; Zheng, Z.-J.; Xu, L.-W. RSC Adv. 2016, 6, 45495.
[11]
(b) Mino, T.; Nishikawa, K.; Asano, M.; Shima, Y.; Ebisawa, T.; Yoshida, Y.; Sakamoto, M. Org. Biomol. Chem. 2016, 14, 7509.
[11]
(c) Yamamoto, K.; Shimizu, T.; Igawa, K.; Tomooka, K.; Hirai, G.; Suemune, H.; Usui, K. Sci. Rep. 2016, 6, 36211.
[11]
(d) Zhang, L.; Xiang, S. H.; Wang, J. J.; Xiao, J.; Wang, J. Q.; Tan, B. Nat. Commun. 2019, 10, 566.
[11]
(e) Mino, T.; Yamaguchi, D.; Masuda, C.; Youda, J.; Ebisawa, T.; Yoshida, Y.; Sakamoto, M. Org. Biomol. Chem. 2019, 17, 145.
[11]
(f) Mino, T.; Yamaguchi, D.; Kumada, M.; Youda, J.; Saito, H.; Tanaka, J.; Yoshida, Y.; Sakamoto, M. Synlett 2021, 32, 532.
[11]
(g) Mino, T.; Fujisawa, Y.; Yoshida, S.; Hirama, M.; Akiyama, T.; Saito, R.; Yoshida, Y.; Kasashima, Y.; Sakamoto, M. Org. Biomol. Chem. 2021, 19, 10385.
[12]
Liu, Z.-S.; Hua, Y.; Gao, Q.; Ma, Y.; Tang, H.; Shang, Y.; Cheng, H.-G.; Zhou, Q. Nat. Catal. 2020, 3, 727.
[13]
Feng, Q.; Ma, X.; Bao, W.; Li, S.-J.; Lan, Y.; Song, Q. CCS Chem. 2021, 3, 377.
[14]
Liu, Y.; Cao, Z.; Du, H. J. Org. Chem. 2012, 77, 4479.
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