Reviews

Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols

  • Zhu Shuai ,
  • Xu Lubin ,
  • Wang Liang ,
  • Xiao Jian
Expand
  • aHubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen 448000;
    b College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109

Received date: 2015-10-21

  Revised date: 2015-12-15

  Online published: 2016-02-01

Supported by

Project supported by the Open Project Program of Hubei Key Laboratory of Drug Synthesis and Optimization Jingchu University of Technology (Nos. OPP2015YB01, OPP2015ZD02), the Talents of High Level Scientific Research Foundation of Qingdao Agricultural University (Nos. 6631112323, 6631115015).

Abstract

The electrophilic intermediate, vinylogous imine or vinylogous iminium, can be in situ generated from 3-indolyl- methanols under acidic conditions. With the aid of chiral catalysts, miscellaneous nucleophiles can attack these electrophilic intermediates to afford enantioenriched and biologically important 3-substituted indole derivatives. The recent advances of preparation of optically active indole derivatives from 3-indolylmethanols via asymmetric alkylation, asymmetric reduction and asymmetric rearrangement are summarized.

Cite this article

Zhu Shuai , Xu Lubin , Wang Liang , Xiao Jian . Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols[J]. Chinese Journal of Organic Chemistry, 2016 , 36(6) : 1229 -1240 . DOI: 10.6023/cjoc201510024

References

[1] Lo, K. K.-W.; Tsang, K. H.-K.; Hui, W.-K.; Zhu, N. Chem. Commun. 2003, 2704.
[2] Plimmer, J. R.; Gammon, D. W.; Ragsdale, N. N. Encyclopedia of Agrochemicals, Vol. 3, John Wiley & Sons, New York, 2003.
[3] Ramirez, A.; Garcia-Rubio, S. Curr. Med. Chem. 2003, 10, 1891.
[4] Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
[5] Goveky, S. P.; Overman, L. E. Tetrahedron 2007, 63, 8499.
[6] (a) Lancianesi, S.; Palmoeri, A.; Petrini, M. Chem. Rev. 2014, 114, 7108.
(b) Shiri, M.; Zolfigol, M. A. Chem. Rev. 2010, 110, 2250.
(c) Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Chem. Soc. Rev. 2010, 39, 4449.
[7] Ramesh, C.; Kavala, V.; Kuo, C. W.; Rama, R. B.; Yao, C. F. Eur. J. Org. Chem. 2010, 2010, 3796.
[8] Furstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed. 2005, 44, 2777.
[9] Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123.
[10] Zhan, Z. P.; Yang, R. F.; Lang, K. Tetrahedron Lett. 2005, 46, 3859.
[11] Auria, M. Tetrahedron 1991, 47, 9225.
[12] Rabindran, S. K.; Ross, D. D.; Doyle, L. A.; Yang, W. D.; Greenberger, L. M. Cancer Res.2000 ,60, 47.
[13] Bergman, J.; Venemalm, L. Tetrahedron Lett. 1988, 29, 2993.
[14] Richou, R. M.; Lallouette, P.; Richou, H. C.R. Acad. Sci. 1967, 264, 2426.
[15] Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123.
[16] Conn, P., M.; Crowley, W. F., Jr. Annu. Rev. Med. 1994, 45, 391.
[17] (a) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed.2009, 48, 9608.
(b) Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Chem. Soc. Rev. 2010, 39, 4449.
(c) Zeng, M.; You, S.-L. Synlett 2010, 1289
[18] (a) Lyttle, D. A.; Weisblat, D. I. J. Am. Chem. Soc. 1947, 69, 2118.
(b) Semenov, B. B.; Granik, V. G. Pharm. Chem. J. 2004, 38, 287.
(c) Palmieri, A.; Petrini, M.; Shaikh, R. R. Org. Biomol. Chem. 2010, 8, 1259.
(d) Wang, L.; Chen, Y.-Y.; Xiao, J. Asian J. Org. Chem. 2014, 3, 1036.
[19] Kataja, A. O.; Masson, G. Tetrahedron 2014, 70, 8783.
[20] Cozzi, P. G.; Benfatti, F.; Zoli, L. Angew. Chem., Int. Ed. 2009, 48, 1313.
[21] Zhang, Y.; Wang, S.-Y.; Xu, X.-P.; Jiang, R.; Ji, S.-J. Org. Biomol. Chem. 2013, 11, 1933.
[22] Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Asian J. 2011, 6, 2890.
[23] (a) Bandini, M.; Tragni, M. Org. Biomol. Chem. 2009, 7, 1501.
(b) Emer, E.; Sinisi, R.; Capdevila, M. G.; Petruzziello, D.; De Vincentiis, F.; Cozzi, P. G. Eur. J. Org. Chem. 2011, 2011, 647.
(c) Cozzi, P.; Gualandi, A. Synlett 2013, 24, 281.
(d) Kumar, R.; Eycken, E. V. V. d. Chem. Soc. Rev. 2013, 42, 1121.
[24] (a) Xiao, J. Org. Lett. 2012, 14, 1716.
(b) Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Commun. 2012, 48, 3548.
[25] Han, B.; Xiao, Y.-C.; Yao, Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 10189.
[26] Xiao, Y.-C.; Zhou, Q.-Q.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2012, 14, 5940.
[27] Xu, B.; Guo, Z. L.; Jin, W. Y.; Wang, Z. P.; Peng, Y. G.; Guo, Q. X. Angew. Chem., Int. Ed. 2012, 51, 1059.
[28] Zhang, C.; Zhang, L.-X.; Qiu, Y.; Xu, B.; Zong, Y.; Guo, Q.-X. RSC Adv. 2014, 4, 6916.
[29] Tan, W.; Li, X.; Gong, Y.-X.; Ge, M.-D.; Shi, F. Chem. Commun. 2014, 50, 15901
[30] Shi, F.; Zhang, H.-H.; Sun, X.-X.; Liang, J.; Fan, T.; Tu, S.-J. Chem. Eur. J. 2015, 21, 3465
[31] Guo, Q.-X.; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620.
[32] Guo, C.; Song, J.; Huang, J.-Z.; Chen, P.-H.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 1046.
[33] Tan, W.; Du, B.-X.; Li, X.; Zhu, X.; Shi, F.; Tu, S.-J. J. Org. Chem. 2014, 79, 4635
[34] Song, J.; Guo, C.; Adele, A.; Yin, H.; Gong, L. Z. Chem. Eur. J. 2013, 19, 3319.
[35] Song, L.; Guo, Q.-X.; Li, X.-C.; Tian, J.; Peng, Y.-G. Angew. Chem., Int. Ed. 2012, 124, 1935.
[36] Ren, C.-L.; Zhang, T.; Wang, X.-Y.; Wu, T.; Ma, J.; Xuan, Q.-Q.; Wei, F.; Huang, H.-Y.; Wang, D.; Liu, L. Org. Biomol. Chem. 2014, 12, 9881.
[37] Guo, Z.-L.; Xue, J.-H.; Fu, L.-N.; Zhang, S.-E.; Guo, Q.-X. Org. Lett. 2014, 16, 6472.
[38] Xu, B.; Shi, L.-L.; Zhang, Y.-Z.; Wu, Z.-J.; Fu, L.-N.; Luo, C.-Q.; Zhang, L.-X.; Peng, Y.-G.; Guo, Q.-X. Chem. Sci. 2014, 5, 1988.
[39] Ma, J.-A.; Dong, X.-D.; Li, S.; Guo, R.; Nie, J. Org. Lett. 2015, 17, 1389.
[40] Shi, F.; Tu, S. J.; Zhu, R.Y. Chem. Eur. J. 2014, 20, 2597.
[41] Dai, W.; Lu, H.; Li, X.; Shi, F.; Tu, S.-J. Chem. Eur. J. 2014, 20, 11382.
[42] Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593.
[43] Zhuo, M.-H.; Jiang, Y.-J.; Fan, Y.-S.; Gao, Y.; Liu, S.; Zhang, S. Org. Lett. 2014, 16, 1096.
[44] Sun, X.-X.; Du, B.-X.; Zhang, H.-H.; Ji, L.; Shi, F. ChemCatChem 2015, 7, 1211.
[45] Sun, F.-L., Gu. Q.; Zeng, M.; You, S.-L. Chem. Eur. J. 2009, 15, 8709.
[46] Wang, S.-G.; Han, L.; Zeng, M.; Sun, F.-L.; Zhang, W.; You, S.-L. Org. Biomol. Chem. 2012, 10, 3202.
[47] Wang, D.-S.; Tang, J.; Zhou, Y.-G.; Chen, M.-W.; Yu, C.-B.; Duan, Y.; Jiang, G.-F. Chem. Sci. 2011, 2, 803.
[48] Duan, Y.; Chen, M.-W.; Ye, Z.-S.; Wang, D.-S.; Chen, Q.-A.; Zhou, Y.-G. Chem. Eur. J. 2011, 17, 7193.
[49] Liang, T.; Zhang, Z.; Antilla, J. C. Angew. Chem., Int. Ed. 2010, 49, 9734.
[50] Non-asymmetric alkylation and arylation of 3-indolylmethanol were implemented in our group under catalyst-free condition with water and trifluoroethanol as reaction media:
(a) Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C.-L.; Wang, C.-Y.; Xiao, J. Adv. Synth. Catal. 2015, 357, 4023.
(b) Xiao, J.; Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C.-L.; Wang, C.-Y. Green Chem. 2016, 18, 1032.

Outlines

/