Chinese Journal of Organic Chemistry >
Construction of Chiral Cyclic Compounds via Asymmetric Cascade[1,n]-Hydride Transfer/Cyclization
Received date: 2017-08-13
Revised date: 2017-09-19
Online published: 2017-10-16
Supported by
Project supported by the Open Project Program of Hubei Key Laboratory of Drug Synthesis and Optimization Jingchu University of Technology (No. OPP2015ZD02) and the Talents of High Level Scientific Research Foundation of Qingdao Agricultural University (No. 6631115015).
The C (sp3)-H adjacent to heteroatoms can be readily functionalized to C-C, C-N, C-O bonds etc. via cascade[1, n]-hydride transfer/cyclization, which shows high potency to construct 5-membered, 6-membered and all carbon rings. This intriguing cascade process can be employed to synthesize common skeletons of significant natural products and pharmaceutical molecules. Chiral amines, Lewis acids and Brønsted acids have been successfully utilized to catalyze the asymmetric cascade reaction.
Xiao Mingyan , Zhu Shuai , Shen Yaobin , Wang Liang , Xiao Jian . Construction of Chiral Cyclic Compounds via Asymmetric Cascade[1,n]-Hydride Transfer/Cyclization[J]. Chinese Journal of Organic Chemistry, 2018 , 38(2) : 328 -340 . DOI: 10.6023/cjoc201708024
[1] (a) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
(b) Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242.
(c) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J. -Q. Chem. Rev. 2017, 117, 8754;(d) Davies, H. M.; Du Bois, J.; Yu, J. Q. Chem. Soc. Rev. 2011, 40, 1855.
(e)Yang, J.; Fu, T.; Long, Y.; Zhou, X. Chin. J. Org. Chem. 2017, 37, 1111(in Chinese). (杨军, 付婷, 龙洋, 周向葛, 有机化学, 2017, 37, 1111.)
[2] (a) Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74.
(b) Li, C. -J. Acc. Chem. Res. 2009, 42, 335.
[3] (a) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322.
[4] Fu, N.; Li, L.; Yang, Q.; Luo, S. Org. Lett. 2017, 19, 2122.
[5] Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069.
[6] (a) Zhang, S.; Zhang, F.; Tu, Y. Chem. Soc. Rev. 2011, 40, 1937.
(b) Guo, S.; Kumar, P. S.; Yang, M. Adv. Synth. Catal. 2017, 359, 2.
(c) Zhang, J. -R.; Xu, L.; Liao, Y. -Y.; Deng, J. -C.; Tang, R. -Y. Chin. J. Chem. 2017, 35, 271.
(d) Shang, X.; Liu, Z. Acta Chim. Sinica 2015, 73, 1275(in Chinese). (尚筱洁, 柳忠全, 化学学报, 2015, 73, 1275.)(e) Liu, L.; Floreancig, P. E. Angew. Chem., Int. Ed. 2010, 49, 5894.
(f) Tu, W.; Floreancig, P. E. Angew. Chem., Int. Ed. 2009, 48, 4567.
(g) Tu, W.; Liu, L.; Floreancig, P. E. Angew. Chem., Int. Ed. 2008, 47, 4184.
[7] (a) Haibach, M. C.; Seidel, D. Angew. Chem., Int. Ed. 2014, 53, 5010.
(b) Peng, B.; Maulide, N. Chem. -Eur. J. 2013, 19, 13274.
(c)Wang, L.; Xiao, J. Adv. Synth. Catal. 2014, 356, 1137.
(d)Wang, L.; Xiao, J. Top. Curr. Chem. 2016, 374, 17.
[8] Pinnow, J. Ber. Dtsch. Chem. Ges. 1895, 28, 3039.
[9] (a) Alajarin, M.; Bonillo, B.; Marin-Luna, M.; Sanchez-Andrada, P.; Vidal, A. Chem. -Eur. J. 2013, 47, 16093.
(b) Zhao, S.; Shu, X.; Ji, K.; Zhou, A.; He, T.; Liu, X.; Liang, Y. J. Org. Chem. 2011, 76, 1941.
(c) Alajarin, M.; Bonillo, B.; Ortin, M. -M.; Sanchez-Andrada, P.; Vidal, A. Eur. J. Org. Chem. 2011, 1896.
(d)Alajarin, M.; Bonillo, B.; Ortin, M.; Sanchez-Andrada, P.; Vidal, A.; Orenes, R. Org. Biomol. Chem. 2010, 8, 4690.
(e)Alajarin, M.; Bonillo, B.; Orenes, R. A.; Ortin, M. M.; Vidal, A. Org. Biomol. Chem. 2012, 10, 9523.
[10] (a) Ruble, J. C.; Hurd, A. R.; Johnson, T. A.; Sherry, D. A.; Barbachyn, M. R.; Toogood, P. L.; Bundy, G. L.; Graber, D. R.; Kamilar, G. M. J. Am. Chem. Soc. 2009, 131, 3991.
(b) Woelfling, J.; Frank, É.; Schneider, G.; Tietze, L. Angew. Chem., Int. Ed. 1999, 38, 200.
(c) Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 1999, 3013.
(d) Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 2004, 90.
[11] Murarka, S.; Zhang, C.; Konieczynska, M. D.; Seidel, D. Org. Lett. 2009, 11, 129.
[12] (a) Mahlau, M.; List, B. Angew. Chem., Int. Ed. 2013, 52, 518.
(b) Du, Y.; Luo, S.; Gong, L. Tetrahedron Lett. 2011, 52, 7064.
[13] Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 6166.
[14] Cao, W.; Liu, X.; Wang, W.; Lin, L.; Feng, X. Org. Lett. 2011, 13, 600.
[15] (a) Chen, L.; Zhang, L.; Lv, J.; Cheng, J.; Luo, S. Chem. -Eur. J. 2012, 18, 8891.
(b) Zhang, L.; Chen, L.; Lv, J.; Cheng, J. -P.; Luo, S. Chem. -Asian J. 2012, 7, 2569.
[16] Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 13226.
[17] Han, Y.; Han, W.; Hou, X.; Zhang, X.; Yuan, W. Org. Lett. 2012, 14, 4054.
[18] Cao, W.; Liu, X.; Guo, J.; Lin, L.; Feng, X. Chem. -Eur. J. 2015, 21, 1632.
[19] Lin, X.; Mao, Z.; Mo, F. Synlett 2015, 27, 546.
[20] Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847.
[21] Suh, C. W.; Kim, D. Y. Org. Lett. 2014, 16, 5374.
[22] Suh, C. W.; Woo, S. B.; Kim, D. Y. Asian J. Org. Chem. 2014, 3, 399.
[23] Kang, Y. K.; Kim, D. Y. Chem. Commun. 2014, 50, 222.
[24] Kang, Y. K.; Kim, D. Y. Adv. Synth. Catal. 2013, 355, 3131.
[25] He, Y. P.; Wu, H.; Chen, D. F.; Yu, J.; Gong, L. Z. Chem. -Eur. J. 2013, 19, 5232.
[26] Suh, C. W.; Kwon, S. J.; Kim, D. Y. Org. Lett. 2017, 19, 1334.
[27] (a) Zhou, G.; Liu, F.; Zhang, J. Chem. -Eur. J. 2011, 17, 3101.
(b) Zhou, G.; Zhang, J. Chem. Commun. 2010, 46, 6593.
[28] Wang, P. F.; Jiang, C. H.; Wen, X.; Xu, Q. L.; Sun, H. J. Org. Chem. 2015, 80, 1155.
[29] Jiao, Z.; Zhang, S.; He, C.; Tu, Y.; Wang, S.; Zhang, F.; Zhang, Y.; Li, H. Angew. Chem., Int. Ed. 2012, 51, 8811.
[30] Liao, S.; Sun, X. L.; Tang, Y. Acc. Chem. Res. 2014, 47, 2260.
[31] Frank, É.; Schneider, G.; Kádár, Z.; Wölfling, J. Eur. J. Org. Chem. 2009, 3544.
/
| 〈 |
|
〉 |
