Research Progress on the Asymmetric Cyclization Synthesis of Seven-Membered Rings via Transition Metal Catalysis

doi:10.6023/cjoc202202005

Abstract

Seven-membered ring skeletons widely exist in many natural products and drug molecules, and it is of great significance to develop efficient asymmetric synthesis methods for seven-membered ring compounds. The progress in the asymmetric synthesis of seven-membered ring compounds by transition metal-catalyzed cycloaddition reactions since 2000 is reviewed. The future development direction of this field is also prospected.

Key words: transition metal catalysis, asymmetric synthesis, seven-membered ring compound

Cite this article

Yuanhao Mao, Yanfeng Gao, Zhiwei Miao. Research Progress on the Asymmetric Cyclization Synthesis of Seven-Membered Rings via Transition Metal Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1904-1924.

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Fig. & Tab. 34

Figure 1. Some examples of natural products and their derivatives with chiral 7-membered rings

Scheme 1. Asymmetric [4+3] cycloaddition reported by Yong Tang’s group and Zuowei Xie’s group in 2015

Scheme 2. Asymmetric [4+3] cycloaddition catalyzed by CuII reported by Chunjiang Wang’s group in 2016

Scheme 3. Asymmetric [4+3] cycloaddition catalyzed by CuI reported by Chunjiang Wang’s group in 2016

Scheme 4. Asymmetric [4+3] cycloaddition reported by Xianxing Jiang’s group and Zhaoqing Xu’s group in 2018

Scheme 5. Asymmetric [4+3] cycloaddition reported by Liuzhu Gong’s group in 2019

Scheme 6. Asymmetric [4+3] cascade annulation reported by Longwu Ye’s group and Chao Deng’s group in 2019 a Conditions: Zn(OTf)2 (20 mol%), L7(24 mol%), Na[BArF4] (30 mol%), DCE, 5 Å MS, r.t., 12 h. b Conditions: Zn(OTf)2 (20 mol%), L7 (24 mol%), Na[BArF4] (30 mol%), DCE, 5 Å MS, 40 °C, 24 h. Na[BArF4]=sodium tetrakis[5-bis(trifluoromethyl)phenyl] borate, DCE=1,2-dichloroethane

Scheme 7. Asymmetric [4+3] cycloaddition reported by Mascareñas’s group in 2007

Scheme 8. Asymmetric [4+3] cycloaddition and [3+2] cycloaddition reported by Mascareñas’s group in 2018

Scheme 9. Some asymmetric examples of the [4+3] cycloaddition reported by Hayashi’s group in 2009 a The reaction was carried out at 20°C. b The reaction was carried out at 40°C

Scheme 10. Asymmetric [4+3] cycloaddition reported by Glorius’s group in 2016

Scheme 11. Asymmetric [5+2] cycloaddition reported by Glorius’s group in 2018

Scheme 12. The transition metal catalyzed [4+3] cycloaddition reported by Feng Shi’s group in 2018

Scheme 13. Asymmetric [4+3] cycloaddition reported by Shuli You’s group in 2019

Scheme 14. (a) (a) Asymmetric [4+3] cycloaddition reported by Weiping Deng’s group and Wulin Yang’s group in 2019; (b) Asymmetric [4+3] cycloaddition reported by Trost’s group in 2019 a Conditions: Pd2(dba)3·CHCl3 (2.5 mol%), L17 (6 mol%), dioxane (0.25 mol/L), r.t., 12 h. b The reaction was carried out at 60 ℃.

Scheme 15. Asymmetric [4+3] cycloaddition reported by Zhihui Shao’s group in 2019

Scheme 16. Asymmetric [4+3] cycloaddition reported by Weiping Deng’s group in 2020

Scheme 17. Asymmetric [5+2] cycloaddition reported by Wenjing Xiao’s group and Liangqiu Lu’s group in 2019

Scheme 18. Asymmetric [5+2] cycloaddition reported by Wenjing Xiao’s group, Liangqiu Lu’s group and Lan Yu’s group in 2020

Scheme 19. Asymmetric [4+3] cycloaddition reported by Weiping Deng’s group and Wulin Yang’s group in 2020 a The reaction was carried out at 0 ℃. b The reaction was carried out at 40 ℃.

Scheme 20. Asymmetric [4+3] cycloaddition reported by Weiping Deng’s group in 2021

Scheme 21. Asymmetric [4+3] cycloaddition reported by Zhiwei Miao’s group in 2021 a The reaction was carried out with the enantiomer of L27.

Scheme 22. Asymmetric [5+2] cycloaddition reported by Wender’s group in 2006 a Reaction was carried out at 50 ℃. b Reaction was carried out at 40~60 ℃ for 8 d.

Scheme 23. Asymmetric [5+2] cycloaddition reported by Hayashi’s group in 2009

Scheme 24. [5+2] cycloaddition via transfer of chirality reported by Junliang Zhang’s group in 2015

Scheme 25. Asymmetric [4+3] cycloaddition reported by Davies’s group in 2014 a A negative sign indicates the enantiomer of 79a. b 2 equiv of 82, hexanes, reflux. c 5 equiv of 80, n-pentane, r.t..

Scheme 26. Asymmetric [4+3] cycloaddition reported by Jiangtao Sun’s group in 2018 a Conditions A: n-hexane/CCl4 (4∶1), 4 Å MS, –35 ℃. b Conditions B: n-hexane/CCl4 (V∶V=4∶1), 4 Å MS, –35 ℃.

Scheme 27. Asymmetric [3+2] cycloaddition reported by Waldmann’s group in 2018

Scheme 28. Asymmetric cascade annulation reported by Shuli You’s group in 2016 and 2017

Scheme 29. Asymmetric [4+3] cycloaddition reported by Yingchun Chen’s group and Wei Du’s group in 2019

Scheme 30. Asymmetric [4+3] cycloaddition reported by Weiping Deng’s group in 2021

Scheme 31. Asymmetric [4+3] cycloaddition reported by Liuzhu Gong’s group in 2021

Scheme 32. Asymmetric [4+3] cycloaddition reported by Mascareñas’s group in 2011 a Combined yield of 112 and 112' upon isolation

Scheme 33. Asymmetric [4+3] cycloaddition reported by Liu and Cheng’s group in 2019

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