Reviews

Recent Development on the Synthetic Methods of Chiral Indoline Derivatives

  • Zhang Baole ,
  • Qin Wei ,
  • Duan Yingchao ,
  • Yu Bin ,
  • Zhang En ,
  • Liu Hongmin
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  • a School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001;
    b School of Pharmacy, Qiqihar Medical University, Qiqihaer 161000

Received date: 2011-11-29

  Revised date: 2012-01-21

  Online published: 2012-03-31

Supported by

Project supported by the National Natural Science Foundation of China (No. 81172937 ), the China Postdoctoral Science Foundation (No. 20100480857), and the Special Financial Grant from the China Postdoctoral Science Foundation (No. 201104402).

Abstract

The indoline skeletons, widely present in alkaloids and other products with diverse biological activities, which also have been considered as privileged structures due to their widespread use as building blocks and chiral auxiliaries in asymmetric synthesis. The importance of these motifs has determined that numerous synthetic multi-step strategies have been developed. Consequently, there has been a continuing interest in the development of efficient methods to obtain enantioenriched substituted indolines. A lot of methods have been introduced, including dynamic kinetic resolution, asymmetric reactions, asymmetric domino cascade reactions and other novel reactions. These methods have been reviewed.

Key words: indoline; asymmetric; synthesis

Cite this article

Zhang Baole , Qin Wei , Duan Yingchao , Yu Bin , Zhang En , Liu Hongmin . Recent Development on the Synthetic Methods of Chiral Indoline Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1359 -1367 . DOI: 10.6023/cjoc1111293

References

[1] Jiang, J.-Z.; Wang, Y. Chin. J. Org. Chem. 2006, 26, 1025 (in Chinese). (蒋金枝, 王艳, 有机化学, 2006, 26, 1025.)

[2] Liu, D.; Zhao, G.; Xiang, L. Eur. J. Org. Chem. 2010, 2010, 3975.

[3] Anas, S.; Kagan, H. B. Tetrahedron: Asymmetry 2009, 20, 2193.

[4] Jin, D.; Zhang, F.; Zhang, D.-C. Chin. J. Org. Chem. 2010, 30, 1005 (in Chinese).(金丹, 张峰, 张德纯, 有机化学, 2010, 30, 1005.)

[5] Liu, J.-Q.; Qian, C.; Chen, X.-Z. Chin. J. Org. Chem. 2011, 31, 634 (in Chinese). (刘金强, 钱超, 陈新志, 有机化学, 2011, 31, 634.)

[6] Orsat, B.; Alper, P. B.; Moree, W.; Mak, C. P.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 712.

[7] Gotor-Fernandez, V.; Fernandez-Torres, P.; Gotor, V. Tetrahedron: Asymmetry 2006, 17, 2558.

[8] Krasnov, V. P.; Levit, G. L.; Andreeva, I. N.; Grishakov, A. N.; Charushin, V. N.; Chupakhin, O. N. Mendeleev Commun. 2002, 12, 27.

[9] Krasnov, V. P.; Levit, G. L.; Bukrina, I. M.; Andreeva, I. N.; Sadretdinova, L. S.; Korolyova, M. A.; Kodess, M. I.; Charushin, V. N.; Chupakhin, O. N. Tetrahedron: Asymmetry 2003, 14, 1985.

[10] Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264.

[11] Hou, X. L.; Zheng, B. H. Org. Lett. 2009, 11, 1789.

[12] Kuwano, R.; Kashiwabara, M.; Sato, K.; Ito, T.; Kaneda, K.; Ito, Y. Tetrahedron: Asymmetry 2006, 17, 521.

[13] Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213.

[14] Kuwano, R.; Kashiwabara, M. Org. Lett. 2006, 8, 2653.

[15] Qiu, L.; Kwong, F. Y.; Wu, J.; Lam, W. H.; Chan, S. S.; Yu, W. Y.; Li, Y. M.; Guo, R. W.; Zhou, Z. Y.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955.

[16] Baeza, A.; Pfaltz, A. Chem. Eur. J. 2010, 16, 2036.

[17] Wang, D. S.; Chen, Q. A.; Li, W.; Yu, C. B.; Zhou, Y. G.; Zhang, X. M. J. Am. Chem. Soc. 2010, 132, 8909.

[18] Yang, S.-X.; Chen, J.; Wu, X.-Y.; Deng, H.-M.; Shao, M.; Zhang, H.; Cao, W.-G. Chin. J. Org. Chem. 2010, 30, 1521 (in Chinese). (杨树新, 陈杰, 吴小余, 邓红梅, 邵敏, 张慧, 曹卫国, 有机化学, 2010, 30, 1521.)

[19] Rueping, M.; Brinkmann, C.; Antonchick, A. P.; Atodiresei, I. Org. Lett. 2010, 12, 4604.

[20] Duan, Y.; Chen, M. W.; Ye, Z. S.; Wang, D. S.; Chen, Q. A.; Zhou, Y. G. Chem. Eur. J. 2011, 17, 7193.

[21] Yip, K. T.; Yang, M.; Law, K. L.; Zhu, N. Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130.

[22] Fuller, P. H.; Kim, J. W.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638.

[23] Yamamoto, H.; Ho, E.; Sasaki, I.; Mitsutake, M.; Takagi, Y.; Imagawa, H.; Nishizawa, M. Eur. J. Org. Chem. 2011, 2011, 2417.

[24] Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438.

[25] Labadie, S. S.; Parmer, C. Synth. Commun. 2011, 41, 1752.

[26] Feltenberger, J. B.; Hsung, R. P. Org. Lett. 2011, 13, 3114.

[27] Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2002, 125, 163.

[28] Viswanathan, R.; Smith, C. R.; Prabhakaran, E. N.; Johnston, J. N. J. Org. Chem. 2008, 73, 3040.

[29] Maciver, E. E.; Thompson, S.; Smith, M. D. Angew. Chem. 2009, 121, 10164.

[30] Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592.

[31] Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314.

[32] Trost, B. M.; Zhang, Y. Chem. Eur. J. 2010, 16, 296.

[33] Franckevi?ius, V.; Cuthbertson, J. D.; Pickworth, M.; Pugh, D. S.; Taylor, R. J. K. Org. Lett. 2011, 13, 4264.

[34] Deboves, H. J. C.; Hunter, C.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. 1 2002, 733.

[35] Minatti, A.; Buchwald, S. L. Org. Lett. 2008, 10, 2721.

[36] Li, J. J.; Mei, T. S.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 6452.

[37] Guthrie, D. B.; Curran, D. P. Org. Lett. 2009, 11, 249.

[38] Bruch, A.; Fr?hlich, R.; Grimme, S.; Studer, A.; Curran, D. P. J. Am. Chem. Soc. 2011, 133, 16270.

[39] Sirasani, G.; Andrade, R. B. Org. Lett. 2011, 13, 4736.

[40] Hélène, P. Tetrahedron 2006, 62, 1619.

[41] Kawasaki, T.; Ogawa, A.; Takashima, Y.; Sakamoto, M. Tetrahedron Lett. 2003, 44, 1591.

[42] García?Ruano, J. L.; Alemán, J.; Catalán, S.; Marcos, V.; Monteagudo, S.; Parra, A.; del?Pozo, C.; Fustero, S. Angew. Chem., Int. Ed. 2008, 47, 7941.

[43] Yip, K. T.; Yang, D. Chem. Asian J. 2011, 42, 2166.
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