过渡金属催化不对称环化反应合成七元环化合物研究进展

doi:10.6023/cjoc202202005

摘要/Abstract

七元环骨架广泛存在于众多天然产物和药物分子中, 发展高效的七元环化合物不对称合成方法具有重要的研究意义. 综述了自2000年以来采用过渡金属催化环加成反应不对称合成七元环化合物研究进展, 并对该领域的研究前景进行了展望.

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

引用此文

毛沅浩, 高延峰, 苗志伟. 过渡金属催化不对称环化反应合成七元环化合物研究进展[J]. 有机化学, 2022, 42(7): 1904-1924.

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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图/表 34

图1. 含有手性七元环结构的天然产物及其衍生物

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

图式1. 唐勇和谢作伟课题组2015年报道的不对称[4+3]环加成反应

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

图式2. 王春江课题组2016年报道的CuII催化的不对称[4+3]环加成反应

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

图式3. 王春江课题组2016年报道的CuI催化的不对称[4+3]环加成反应

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

图式4. 蒋先兴课题组和许兆青课题组2018年报道的不对称[4+3]环加成反应

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

图式5. 龚流柱课题组在2019年报道的不对称[4+3]环加成反应

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

图式6. 叶龙武课题组和邓超课题组在2019年报道的不对称[4+3]串联环化反应

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

图式7. Mascareñas课题组2007年报道的不对称[4+3]环加成反应

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

图式8. Mascareñas课题组2018年报道的不对称[4+3]环加成和[3+2]环加成反应

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

图式9. Hayashi课题组在2009年报道的[4+3]环加成反应的不对称实例

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

图式10. Glorius课题组2016年报道的不对称[4+3]环加成反应

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

图式11. Glorius课题组2018年报道的不对称[5+2]环加成反应

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

图式12. 石枫课题组在2018年报道的过渡金属催化的[4+3]环加成反应

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

图式13. 游书力课题组2019年报道的不对称[4+3]环加成反应

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

图式14. (a)邓卫平课题组和杨武林课题组2019年报道的不对称[4+3]环加成反应; (b) Trost课题组2019年报道的不对称[4+3]环加成反应

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 ℃.

图式15. 邵志会课题组在2019年报道的不对称[4+3]环加成反应

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

图式16. 邓卫平课题组在2020年报道的不对称[4+3]环加成反应

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

图式17. 肖文精课题组和陆良秋课题组2019年报道的不对称[5+2]环加成反应

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

图式18. 肖文精课题组、陆良秋课题组和蓝宇课题组2020年报道的不对称[5+2]环加成反应

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

图式19. 邓卫平课题组和杨武林课题组2020年报道的不对称[4+3]环加成反应

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 ℃.

图式20. 邓卫平课题组2021年报道的不对称[4+3]环加成反应

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

图式21. 苗志伟课题组2021年报道的不对称[4+3]环加成反应

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.

图式22. Wender课题组2006年报道的不对称[5+2]环加成反应

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.

图式23. Hayashi课题组2009年报道的不对称[5+2]环加成反应

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

图式24. 张俊良课题组2015年报道的手性转移的[5+2]环加成反应

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

图式25. Davies课题组2014年报道的不对称[4+3]环加成反应

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..

图式26. 孙江涛课题组2018年报道的不对称[4+3]环加成反应

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 ℃.

图式27. Waldmann课题组在2018年报道的不对称[3+2]环加成反应

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

图式28. 游书力课题组在2016年和2017年报道的不对称串联环化反应

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

图式29. 陈应春课题组和杜玮课题组2019年报道的不对称[4+3]环加成反应

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

图式30. 邓卫平课题组在2021年报道的不对称[4+3]环加成反应

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

图式31. 龚流柱课题组2021年报道的不对称[4+3]环加成反应

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

图式32. Mascareñas课题组2011年报道的不对称[4+3]环加成反应

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

图式33. Liu和Cheng课题组在2019年报道的不对称[4+3]环加成反应

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

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