Reviews

Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Azabicyclic Alkenes

  • Cheng Hanchao ,
  • Liang Xiuli ,
  • Li Xiaolu ,
  • Long Yuhua ,
  • Yang Dingqiao
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  • School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2011-06-22

  Revised date: 2011-09-30

  Online published: 2012-03-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172081) and the Natural Science Foundation of Guangdong Province (No. 8251063101000002).

Abstract

The recent progress in transition metal-catalyzed ring-opening reactions of azabicyclic alkenes was reviewed focused on the influence of the types of transition metal catalysts, nucleophiles, ligands, the structures of azabicyclic alkenes and its derivatives, solvents and additives on the ring-opening reactions. Moreover, the possible mechanisms of the ring-opening reactions were also discussed.

Cite this article

Cheng Hanchao , Liang Xiuli , Li Xiaolu , Long Yuhua , Yang Dingqiao . Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Azabicyclic Alkenes[J]. Chinese Journal of Organic Chemistry, 2012 , (03) : 433 -443 . DOI: 10.6023/cjoc1106222

References

[1] Scott, E. S.; Felix, A. A.; Ratna, C.; David, E. N.; Val, J. W.; Richard,B. M. J. Med. Chem. 1995, 38, 2395.  

[2] Roberto, P.; Francesco, B.; Nicola, C. A.; Marcello, L.; Vincenzo,T.; Francesco, F.; Vincenzo, O.; Alberto, G.; Stefano, G. J. Med.Chem. 1995, 38, 942.  

[3] Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211.  

[4] Kamal, A.; Gayatri, N. L. Tetrahedron Lett. 1996, 37, 3359.  

[5] Sobti, A.; Kim, K.; Sulikowski, G. A. J. Org. Chem. 1996, 61, 6.  

[6] Johnson, B. M.; Chang, P. T. L. Anal. Profiles Drug Subst. Excipients1996, 24, 443.  

[7] Murakami, M.; Lgawa, H. Chem. Commun. 2002, 4, 390.

[8] Degnan, A. P.; Meyers, A. I. J. Org. Chem. 2000, 65, 3503.  

[9] Wu, M.-S.; Jeganmohan, M.; Cheng, C.-H. J. Org. Chem. 2005, 70,9545.  

[10] Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2006,8, 621.  

[11] Alexakis, A.; Hajjaji, S. E.; Polet, D.; Rathgeb, X. Org. Lett. 2007,9, 3393.  

[12] Lautens, M.; Fagnou, K. Proc. Natl. Acad. Sci. U. S. A. 2004, 101,5455.

[13] Rayabarapu, D. K.; Cheng, C.-H. Acc. Chem. Res. 2003, 36, 48.  

[14] Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.  

[15] Feng, C.-C.; Nandi, M.; Sambaiah, T.; Cheng, C.-H. J. Org. Chem.1999, 64, 3538.  

[16] Rayabarapu, D. K.; Shukla, P.; Cheng, C.-H. Org. Lett. 2003, 5,4903.  

[17] Rayabarapu, D. K.; Chiu, C.-F.; Cheng, C.-H. Org. Lett. 2002, 4,1679.  

[18] Rayabarapu, D. K.; Cheng, C.-H. Chem. Eur. J. 2003, 9, 3164.  

[19] Wu, M.-S.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004,

[20] Li, L.-P.; Rayabarapu, D. K.; Nandi, M.; Cheng, C.-H. Org. Lett.2003, 5, 1621.  

[21] Lautens, M.; Fagnou, K. Tetrahedron 2001, 57, 5067.  

[22] Array, R. G.; Cabrera, S.; Carreterro, J. C. Org. Lett. 2005, 7,219.  

[23] Array, R. G.; Cabrera, S.; Carreterro, J. C. Synthesis 2006, 1205.

[24] Pineschi, M.; Moro, F. D.; Crotti, P.; Macchia, F. Org. Lett. 2005,7, 3605.  

[25] Villeneuve, K.; Tam, W. J. Am. Chem. Soc. 2006, 128, 3514.  

[26] Burton, R. R.; Tam, W. Org. Lett. 2007, 9, 3287.  

[27] Tenaglia, A.; Marc, S. J. Org. Chem. 2008, 73, 1397.  

[28] Cortez, G. A.; Baxter, C. A.; Schrock, R. R.; Hoveyda, A. H. Org.Lett. 2007, 9, 2871.  

[29] Carreras, J.; Avenoza, A.; Busto, J. H.; Peregrina, J. M. Org. Lett.2007, 9, 1235.  

[30] Lautens, M.; Fagnou, K.; Zunic, V. Org. Lett. 2002, 4, 3465.  

[31] Cho, Y.-H.; Zunic, V.; Senboku, H.; Olsen, M.; Lautens, M. J. Am.Chem. Soc. 2006, 128, 6837.  

[32] Cho, Y.-H.; Fayol, A.; Lautens, M. Tetrahedron: Asymmetry 2006,17, 416.  

[33] Xie, L.; Yang, D.-Q.; Zhao, S.-Q.; Wang, H.; Liang, L.-H.; Luo,R.-S. Chem. Lett. 2007, 18, 127.

[34] Long, Y.-H.; Yang, D.-Q.; Zeng, H.-P.; Xie, L.; Wu, L.-H.; Mo,H.-H.; Zuo, X.-J. Chin. J. Chem. 2010, 28, 235.

[35] Menard, F.; Weise, C. F.; Lautens, M. Org. Lett. 2007, 9, 5365.  

[36] Menard, F.; Lautens, M. Angew. Chem., Int. Ed. 2008, 47, 2085.  

[37] Nishimura, T.; Tsurumaki, E.; Kawamoto, T.; Guo, X.-X.; Hayashi,T. Org. Lett. 2008, 10, 4057.

[38] Yang, D.-Q.; Long, Y.-H.; Wang, H.; Zhang, Z.-M. Org. Lett.2008, 10, 4723.  

[39] (a) Long, Y.-H.; Yang, D.-Q.; Zhang, Z.-M.; Wu, Y.-J.; Zeng,H.-P.; Chen, Y. J. Org. Chem. 2010, 75, 7291.(b) Yang, D.-Q.; Long, Y.-H.; Wu, Y.-J.; Zuo, X.-J.; Tu, Q.-Q.;Fang, S.; Jiang, L.-S.; Wang, S.-Y.; Li. C.-R. Organometallics2010, 29, 5936.  

[40] Lautens, M.; Hiebert, S.; Renaud, J. Org. Lett. 2000, 2, 1971.  

[41] Cabrera, S.; Array, R. G.; Alonso, I.; Carretero, J. C. J. Am.Chem. Soc. 2005, 127, 17938.  

[42] Ogura, T.; Yoshida, K.; Yanagisawa, A.; Imamoto, T. Org. Lett.2009, 11, 2245.  

[43] John, J.; Anas, S.; Sajisha, V. S.; Viji, S.; Radhakrishnan, K. V.Tetrahedron Lett. 2007, 48, 7225.  

[44] John, J.; Adarsh, B.; Radhakrishnan, K. V. Tetrahedron 2010, 66,1383.  

[45] Lautens, M.; Dockendorff, C. Org. Lett. 2003, 5, 3695.  

[46] Chen, C. L.; Martin, S. F. J. Org. Chem. 2006, 71, 4810.  

[47] Rayabarapu, D. K.; Cheng, C.-H. Acc. Chem. Res. 2007, 40, 971.  
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