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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 1: 221 - 227

DOI: https://doi.org/10.6023/cjoc201708002

Articles

Asymmetric Synthesis of Methyl N-(tert-Butoxycarbonyl)indoline-2-carboxylates

  • Zhang Qianqian ,
  • Ding Qunshan ,
  • Song Chuanjun ,
  • Chang Junbiao
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  • a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
    b Collaborative Innovation Centre of New Drug Research and Safety Evaluation of Henan Province, Zhengzhou 450001

Received date: 2017-08-01

  Revised date: 2017-08-31

  Online published: 2017-09-08

Supported by

Project supported by the Natural Science Foundation of China (Nos. 81330075, 21172202).

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Abstract

As a characteristic structural motif of numerous biologically active natural products and new drugs, chiral indoline derivatives have attracted much attention of chemists. Although many methods are available, there is still great need to develop a new, simple and highly efficient asymmetric synthetic method of indoline derivatives. Starting from Williams chiral auxiliary, a variety of methyl (R)-N-(tert-butoxycarbonyl)indoline-2-carboxylates were obtained with high overall yields and enantioselectivity through nucleophilic substitution, intramolecular Buchwald-Hartwig coupling reaction, etc.

Key words： indoline-2-carboxylate; Williams chiral auxiliary; Buchwald-Hartig coupling; asymmetric synthesis

Cite this article

Zhang Qianqian , Ding Qunshan , Song Chuanjun , Chang Junbiao . Asymmetric Synthesis of Methyl N-(tert-Butoxycarbonyl)indoline-2-carboxylates[J]. Chinese Journal of Organic Chemistry, 2018 , 38(1) : 221 -227 . DOI: 10.6023/cjoc201708002

References

[1] Bonjoch, J.; Solé, D.; García-Rubio, S.; Bosch, J. J. Am. Chem. Soc. 1997, 119, 7230.
[2] Zhang, D.; Song, H.; Qin, Y. Acc. Chem. Res. 2011, 44, 447.
[3] Deng, X.; Liang, K.; Tong, X.; Ding, M.; Zhou, A.; Xia, C. Org. Lett. 2014, 16, 3276.
[4] Wang, T.; Xu, Q.; Yu, P.; Liu, X.; Cook, J. Org. Lett. 2001, 3, 345.
[5] Fu, X.; Cook, J. M. J. Am. Chem. Soc. 1992, 114, 6910.
[6] Li, J.; Wang, T.; Yu, P.; Peterson, A.; Weber, R.; Soerens, D.; Grubisha, D.; Bennett, D.; Cook, J. M. J. Am. Chem. Soc. 1999, 121, 6998.
[7] Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Tetrahedron 2005, 61, 2075.
[8] Toda, N.; Ori, M.; Takami, K.; Tago, K.; Kogen, H. Org. Lett. 2003, 5, 269.
[9] Langlois, N.; Gueritte, F.; Langlois, Y.; Potier, P. J. Am. Chem. Soc. 1976, 98, 7017.
[10] Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523.
[11] Marino, J. P.; Rubio, M. B.; Cao, G.; Dios, A. J. Am. Chem. Soc. 2002, 124, 13398.
[12] Iyengar, R.; Schildknegt, K.; Morton, M.; Aubé, J. J. Org. Chem. 2005, 70, 10645.
[13] Rakhit, A.; Hurley, M. E.; Tipnis, V.; Coleman, J.; Rommel, A.; Brunner, H. R. J. Clin. Pharm. 1986, 26, 156.
[14] Anas, S.; Kagan, H. B. Tetrahedron: Asymmetry 2009, 20, 2193.
[15] Zhang, L. B.; Qin, W.; Duan, Y. C.; Yu, B.; Zhang, E.; Liu, H. M. Chin. J. Org. Chem. 2012, 32, 1359(in Chinese).(张宝乐, 秦伟, 段迎超, 余斌, 张恩, 刘宏民, 有机化学, 2012, 32, 1359.)
[16] Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103.
[17] Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547.
[18] Zhai, W. Tetrahedron 1988, 44, 5425.
[19] Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501.
[20] Williams, R. M.; Hendrix, J. A. J. Org. Chem. 1990, 55, 3723.
[21] Williams, R. M.; Im, M. N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976.
[22] Williams, R. M.; Fegley, G. J. J. Org. Chem. 1993, 58, 6933.
[23] Song, C.; Tapaneeyakorn, S.; Murphy, A. C.; Butts, C.; Watts, A.; Willis, C. L. J. Org. Chem. 2009, 74, 8980.
[24] Williams, R. M. J. Org. Chem. 2011, 76, 4221.
[25] Yang, P. Y.; Zhou, Y. G. Tetrahedron: Asymmetry 2004, 15, 1145.
[26] Looper, R. E.; Williams, R. M. Tetrahedron Lett. 2001, 42, 769.
[27] Looper, R. E.; Runnegar, M. T. C.; Williams, R. M. Tetrahedron 2006, 62, 4549.
[28] Looper, R. E.; Williams, R. M. Angew. Chem., Int. Ed. 2004, 43, 2930.
[29] Looper, R. E.; Runnegar, M. T. C.; Williams, R. M. Angew. Chem., Int. Ed. 2005, 44, 3879.
[30] Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
[31] Onishi, T.; Sebahar, P. R.; Williams, R. M. Tetrahedron 2004, 60, 9503.
[32] Ahrendt, K. A.; Williams, R. M. Org. Lett. 2004, 6, 4539.
[33] Jain, R. P.; Williams, R. M. Tetrahedron Lett. 2001, 42, 4437.
[34] Jain, R. P.; Williams, R. M. Tetrahedron 2001, 57, 6505.
[35] Schuber, P. T.; Williams, R. M. Tetrahedron Lett. 2012, 53, 380.
[36] Zhao, Y.; Liu, L.; Sun, W.; Lu, J.; McEachern, D.; Li, X.; Yu, S.; Bernard, D.; Ochsenbein, P.; Ferey, V.; Carry, J. C.; Dechamps, J. R.; Sun, D.; Wang, S. J. Am. Chem. Soc. 2013, 135, 7223.
[37] Kurokawa, M.; Sugai, T. Bull. Chem. Soc. Jpn. 2004, 77, 1021.

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