可见光催化环丙基胺与1,2-二酮衍生物的[3+2]环加成反应
收稿日期: 2019-02-21
修回日期: 2019-03-27
网络出版日期: 2019-04-11
基金资助
国家自然科学基金(No.21572184)、福建省自然科学基金(No.2017J06006)、中央高校基本科研业务费(No.20720160027)资助项目.
Visible-Light-Induced[3+2] Annulation of Cyclopropylamines with 1,2-Diketone Derivatives
Received date: 2019-02-21
Revised date: 2019-03-27
Online published: 2019-04-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21572184), the Natural Science Foundation of Fujian Province (No. 2017J06006), and the Fundamental Research Funds for the Central Universities (No. 20720160027).
报道了一种可见光催化环丙基胺与1,2-二芳基乙二酮衍生物的[3+2]环加成反应,合成了一系列α-氨基呋喃衍生物,该反应条件温和,产率良好,操作简单.这一方法为潜在生物活性分子骨架α-氨基呋喃衍生物的合成提供了一条高效便捷的路径.
关键词: 光氧化还原; 环丙基胺; 1,2-二酮衍生物; [3+2]环加成反应
代雪梅 , 李延军 , 张少南 , 龚磊 . 可见光催化环丙基胺与1,2-二酮衍生物的[3+2]环加成反应[J]. 有机化学, 2019 , 39(6) : 1711 -1719 . DOI: 10.6023/cjoc201902022
A visible-light-induced[3+2] annulation of arylcyclopropylamines and 1,2-diarylethanediones was report. A series of α-amino tetrahydrofuran derivatives were synthesized in moderate to good isolated yields under mild reaction conditions. This method would provide an efficient and convenient approach to α-amino tetrahydrofurans which are potentially important buiding blocks in bioactive compounds.
Key words: photoredox; cyclopropylamines; 1,2-diketone derivatives; [3+2] annulation
[1] Cheng, X. H.; Hii, K. K. Tetrahedron 2001, 57, 5445.
[2] Kunz, K. R.; Iyengar, B. S.; Dorr, R. T.; Alberts, D. S.; Remers, W. A. J. Med. Chem. 1991, 34, 2281.
[3] Lockhoff, O.; Stadler, P. Carbohydr. Res. 1998, 314, 13.
[4] Takeuchi, Y.; Chang, M. R.; Hashigaki, K.; Yamato, M. Chem. Pharm. Bull. 1991, 39, 1629.
[5] (a) Eliel, E. L.; Daignault, R. A. J. Org. Chem. 1965, 30, 2450~2451.
(b) Glacet, C.; Veron, D. Bull. Soc. Chim. Fr. 1965, 1789.
[6] For selected reviews on visible-light photoredox catalysis, see:
(a) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
(b) Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828.
(c) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687.
(d) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387.
(e) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
(f) Dai, X. J.; Xu, X. L.; Li, X. N. Chin. J. Org. Chem. 2013, 33, 2406 (in Chinese).(戴小军, 许孝良, 李小年, 有机化学, 2013, 33, 2406.)
(g) Guan, B. C.; Xu, X. L.; Wang, H; Li, X. N. Chin. J. Org. Chem. 2016, 36, 1564 (in Chinese).(关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
(h) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
(i) Skubi, K. L.; Blum, T. R.; Yoon. T. P. Chem. Rev. 2016, 116, 10035.
(j) Nakajima, K.; Miyake, Y.; Nishibayashi, Y. Acc. Chem. Res. 2016, 49, 1946.
(k) Liu, W.; Zheng, X. Y.; Zeng, J. G.; Cheng, P. Chin. J. Org. Chem. 2017, 37, 1 (in Chinese).(刘薇, 郑昕宇, 曾建国, 程辟, 有机化学, 2017, 37, 1.)
(l) Ruan, L. H.; Dong, Z. C.; Chen, C. X.; Wu, S.; Sun, J. Chin. J. Org. Chem. 2017, 37, 2544 (in Chinese).(阮利衡, 董振诚, 陈春欣, 吴爽, 孙京, 有机化学, 2017, 37, 2544.)
(m) Dai, X. Q.; Zhu, Y. B.; Xu, X. L.; Weng, J. Q. Chin. J. Org. Chem. 2017, 37, 577 (in Chinese).(戴小强, 朱亚波, 许孝良, 翁建全, 有机化学, 2017, 37, 577.)
(n) Xu, W. X.; Dai, X. Q; Xu, H. J.; Weng, J. Q. Chin. J. Org. Chem. 2018, 38, 2807 (in Chinese).(徐雯秀, 戴小强, 徐涵靖, 翁建全, 有机化学, 2018, 38, 2807.)
(o) Bai, Q. F.; He, J. Y.; Zhu, X. Q.; Feng, G. F.; Jin, C. A. Chin. J. Org. Chem. 2019, 39, 527 (in Chinese).(白其凡, 何静耀, 祝小青, 冯高峰, 金城安, 有机化学, 2019, 39, 527.)
[7] For examples of visible-light photoredox catalysis, see:
(a) Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
(b) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
(c) Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735.
(d) Alonso, R.; Bach, T. Angew. Chem., Int. Ed. 2014, 53, 4368.
(e) Huo, H. H.; Shen, X. D.; Wang, C. Y.; Zhang, L. L.; Rose, P.; Chen, L. A.; Harms, K.; Marsch, M.; Hilt, G.; Meggers, E. Nature 2014, 515, 100.
(f) Espelt, L. R.; McPherson, I. S.; Wiensch, E. M. Yoon, T. P. J. Am. Chem. Soc. 2015, 137, 2452.
(g) Ding, W.; Lu, L. Q.; Zhou, Q. Q.; Wei, Y.; Chen, J. R.; Xiao, W. J. J. Am. Chem. Soc. 2017, 139, 63.
(h) Ding, W.; Lu, L. Q.; Zhou, Q. Q.; Wei, Y.; Chen, J. R.; Xiao, W. J. J. Am. Chem. Soc. 2017, 139, 63.
(i) Zhou, Q. Q.; Liu, D.; Xiao, W. J.; Lu, L. Q. Acta Chim. Sinica 2017, 75, 110 (in Chinese).(周泉泉, 刘丹, 肖文精, 陆良秋, 化学学报, 2017, 75, 110.)
(j) Wu, Z. J.; Wang, J. Acta Chim. Sinica 2017, 75, 74 (in Chinese).(吴自俊, 汪舰, 化学学报, 2017, 75, 74.)
(k) Wu, J.; Li, J. W.; Li, H.; Zhu, C. Y. Chin. J. Org. Chem. 2017, 37, 2203 (in Chinese).(吴江, 李嘉雯, 李昊, 朱纯银, 有机化学, 2017, 37, 2203.)
(l) Ye, H; Xiao, C; Lu, L. Q. Chin. J. Org. Chem. 2018, 38, 1897 (in Chinese).(叶辉, 肖聪, 陆良秋, 有机化学, 2018, 38, 1897.)
[8] (a) Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672.
(b) Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338.
(c) Espelt, L. R.; McPherson, I. S.; Wiensch, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2015, 137, 2452.
[9] Tan, Y. Q.; Yuan, W.; Gong, L.; Meggers, E. Angew. Chem., Int. Ed. 2015, 54, 13045.
[10] (a) Maity, S.; Zhu, M. Z.; Shinabery, R. S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 222.
(b) Nguyen, T. H.; Maity, S.; Zheng, N. Beilstein J. Org. Chem. 2014, 10, 975.
(c) Staveness, D.; Sodano, T. M.; Li, K. J.; Burnham, E. A.; Jackson, K. D.; Stephenson, C. R. J. Chem 2019, 5, 1.
[11] (a) Russell, G. A.; Weiner, S. A. J. Am. Chem. Soc. 1967, 89, 6623.
(b) Ma, J. J.; Rosales, A. R.; Huang, X. Q.; Harms, K.; Riedel R.; Wiest, O.; Meggers, E. J. Am. Chem. Soc. 2017, 139, 17245.
[12] Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[13] Reger, D.; Haines P.; Heinemann, F. W.; Guldi, D. M.; Jux, N. Angew. Chem., Int. Ed. 2018, 57, 5938.
[14] Cui, W.; Loeppky, R. N. Tetrahedron 2001, 57, 2953.
/
| 〈 |
|
〉 |