Citation: 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 shu

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

  • Corresponding author: Wang Liang, chemjianxiao@163.com Xiao Jian, chemjianxiao@163.com
  • Received Date: 21 October 2015
    Revised Date: 15 December 2015

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

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  • 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.
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    1. [1]

    2. [2]

      Plimmer, J. R.; Gammon, D. W.; Ragsdale, N. N. Encyclopedia of Agrochemicals, Vol. 3, John Wiley & Sons, New York, 2003.

    3. [3]

      Ramirez, A.; Garcia-Rubio, S. Curr. Med. Chem. 2003, 10, 1891.

    4. [4]

      Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489. 

    5. [5]

      Goveky, S. P.; Overman, L. E. Tetrahedron 2007, 63, 8499. 

    6. [6]

      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. [7]

      Ramesh, C.; Kavala, V.; Kuo, C. W.; Rama, R. B.; Yao, C. F. Eur. J. Org. Chem. 2010, 2010, 3796. 

    8. [8]

      Furstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed. 2005, 44, 2777. 

    9. [9]

      Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123.

    10. [10]

      Zhan, Z. P.; Yang, R. F.; Lang, K. Tetrahedron Lett. 2005, 46, 3859. 

    11. [11]

      Auria, M. Tetrahedron 1991, 47, 9225.

    12. [12]

      Rabindran, S. K.; Ross, D. D.; Doyle, L. A.; Yang, W. D.; Greenberger, L. M. Cancer Res.2000 ,60, 47.

    13. [13]

      Bergman, J.; Venemalm, L. Tetrahedron Lett. 1988, 29, 2993. 

    14. [14]

      Richou, R. M.; Lallouette, P.; Richou, H. C.R. Acad. Sci. 1967, 264, 2426.

    15. [15]

      Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123.

    16. [16]

      Conn, P., M.; Crowley, W. F., Jr. Annu. Rev. Med. 1994, 45, 391. 

    17. [17]

      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. [18]

      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. [19]

      Kataja, A. O.; Masson, G. Tetrahedron 2014, 70, 8783. 

    20. [20]

      Cozzi, P. G.; Benfatti, F.; Zoli, L. Angew. Chem., Int. Ed. 2009, 48, 1313. 

    21. [21]

      Zhang, Y.; Wang, S.-Y.; Xu, X.-P.; Jiang, R.; Ji, S.-J. Org. Biomol. Chem. 2013, 11, 1933.

    22. [22]

      Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Asian J. 2011, 6, 2890.

    23. [23]

      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. [24]

      Xiao, J. Org. Lett. 2012, 14, 1716. (b) Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Commun. 2012, 48, 3548.

    25. [25]

      Han, B.; Xiao, Y.-C.; Yao, Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 10189.

    26. [26]

      Xiao, Y.-C.; Zhou, Q.-Q.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2012, 14, 5940.

    27. [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. [28]

      Zhang, C.; Zhang, L.-X.; Qiu, Y.; Xu, B.; Zong, Y.; Guo, Q.-X. RSC Adv. 2014, 4, 6916.

    29. [29]

      Tan, W.; Li, X.; Gong, Y.-X.; Ge, M.-D.; Shi, F. Chem. Commun. 2014, 50, 15901

    30. [30]

      Shi, F.; Zhang, H.-H.; Sun, X.-X.; Liang, J.; Fan, T.; Tu, S.-J. Chem. Eur. J. 2015, 21, 3465

    31. [31]

      Guo, Q.-X.; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620.

    32. [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. [33]

      Tan, W.; Du, B.-X.; Li, X.; Zhu, X.; Shi, F.; Tu, S.-J. J. Org. Chem. 2014, 79, 4635

    34. [34]

      Song, J.; Guo, C.; Adele, A.; Yin, H.; Gong, L. Z. Chem. Eur. J. 2013, 19, 3319. 

    35. [35]

      Song, L.; Guo, Q.-X.; Li, X.-C.; Tian, J.; Peng, Y.-G. Angew. Chem., Int. Ed. 2012, 124, 1935.

    36. [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. [37]

      Guo, Z.-L.; Xue, J.-H.; Fu, L.-N.; Zhang, S.-E.; Guo, Q.-X. Org. Lett. 2014, 16, 6472.

    38. [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. [39]

      Ma, J.-A.; Dong, X.-D.; Li, S.; Guo, R.; Nie, J. Org. Lett. 2015, 17, 1389.

    40. [40]

      Shi, F.; Tu, S. J.; Zhu, R.Y. Chem. Eur. J. 2014, 20, 2597. 

    41. [41]

      Dai, W.; Lu, H.; Li, X.; Shi, F.; Tu, S.-J. Chem. Eur. J. 2014, 20, 11382.

    42. [42]

      Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593. 

    43. [43]

      Zhuo, M.-H.; Jiang, Y.-J.; Fan, Y.-S.; Gao, Y.; Liu, S.; Zhang, S. Org. Lett. 2014, 16, 1096.

    44. [44]

      Sun, X.-X.; Du, B.-X.; Zhang, H.-H.; Ji, L.; Shi, F. ChemCatChem 2015, 7, 1211.

    45. [45]

      Sun, F.-L., Gu. Q.; Zeng, M.; You, S.-L. Chem. Eur. J. 2009, 15, 8709.

    46. [46]

      Wang, S.-G.; Han, L.; Zeng, M.; Sun, F.-L.; Zhang, W.; You, S.-L. Org. Biomol. Chem. 2012, 10, 3202.

    47. [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. [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. [49]

      Liang, T.; Zhang, Z.; Antilla, J. C. Angew. Chem., Int. Ed. 2010, 49, 9734. 

    50. [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. 

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