Reviews

Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Oxa(Aza)bicyclic Alkenes with Carbanion Nucleophiles

  • Wu Ruihua ,
  • Yang Wen ,
  • Cheng Guo ,
  • Li Yue ,
  • Yang Dingqiao
Expand
  • Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2016-04-03

  Revised date: 2016-05-17

  Online published: 2016-06-02

Supported by

Project supported by the National Natural Science Foundation of China (Nos.21172081, 21372090), the Natural Science Foundation of Guangdong Province (No.S2013020013091) and the City of Guangzhou Science and Technology Plan Projects (No.156300018).

Abstract

The recent progress in transition metal-catalyzed asymmetric ring-opening reactions of oxa(aza)bicyclic alkenes with carbanion nucleophiles is reviewed with focus on the influence of the types of transition metal catalysts, carbanion nucleophiles, ligands, the structures of oxa(aza)bicyclic alkenes, solvents and additives on the asymmetric ring-opening reactions. Moreover, the parties of possible mechanisms for the asymmetric ring-opening reactions are also discussed.

Cite this article

Wu Ruihua , Yang Wen , Cheng Guo , Li Yue , Yang Dingqiao . Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Oxa(Aza)bicyclic Alkenes with Carbanion Nucleophiles[J]. Chinese Journal of Organic Chemistry, 2016 , 36(10) : 2368 -2379 . DOI: 10.6023/cjoc201604006

References

[1] Snyder, S. E.; Felix, A. A.; Chakraborti, R.; Nichols, D. E.; Watts, V. J.; Mailman, R. B. J. Med. Chem. 1995, 38, 2395.
[2] Perrone, R.; Berardi, F.; Colabufo, N. A.; Leopoldo, M.; Tortorella, V.; Fiorentini, F.; Olgiati, V.; Ghiglieri, A.; Govonig, S. J. Med. Chem. 1995, 38, 942.
[3] Pineschi, M. New J. Chem. 2004, 28, 657.
[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. Anal. Profiles Drug Subst. Excipients 1996, 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.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
[13] Lautens, M.; Fagnou, K. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5455.
[14] Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
[15] (a) Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437. (b) Li, M.; Yan, X.-X.; Hong, W.; Zhu, X.-Z.; Cao, B.-X.; Sun, J.; Hou, X.-L. Org. Lett. 2004, 6, 2833.
[16] (a) Arrayas, R. G.; Cabrera, S.; Carretero, J. Org. Lett. 2003, 5, 1333. (b) Zhang, W.; Wang, L.-X.; Shi, W.-J.; Zhou, Q.-L. J. Org. Chem. 2005, 70, 3734.
[17] (a) Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 131. (b) Lautens, M.; Dockendorff, C. Org. Lett. 2003, 5, 3695.
[18] Chen, H.-L.; Li, S.-F.; Xu, J.-B.; Yang, Q.-J.; Liu, S.-S.; Zhou, Y.-Y.; Huang, C.; Fan, B.-M. Acta Chim. Sinica 2013, 71, 1243(in Chinese). (陈花磊, 李嗣锋, 徐建斌, 杨清镜, 刘珊珊, 周永云, 黄超, 樊保敏, 化学学报, 2013, 71, 1243.)
[19] Yang, D.-Q.; Han, Y.-F. Chin. J. Org. Chem. 2006, 26, 1613(in Chinese). (杨定乔, 韩英锋, 有机化学, 2006, 26, 1613.)
[20] Cheng, H.-C.; Liang, X.-L.; Li, X.-L.; Long, Y.-H.; Yang, D.-Q. Chin. J. Org. Chem. 2012, 32, 433(in Chinese). (程汉超, 梁秀丽, 李晓璐, 龙玉华, 杨定乔, 有机化学, 2012, 32, 433.)
[21] Imamoto, T.; Sugita, K.; Yoshida, K. J. Am. Chem. Soc. 2005, 127, 11934.
[22] Cabrera, S.; Arrayas, R. G.; Alonso, I.; Carretero,. C. J. Am. Chem. Soc. 2005, 127, 17938.
[23] Zhang, T.-K.; Yuan, K.; Hou, X.-L. J. Org. Chem. 2007, 692, 1912.
[24] Imamoto, T.; Saitoh, Y.; Koide, A.; Ogura, T.; Yoshida, K. Angew. Chem., Int. Ed. 2007, 46, 8636.
[25] Endo, K.; Tanaka, K.; Ogawa, M.; Shibata, T. Org. Lett. 2011, 13, 868.
[26] Chen, C.-L.; Martin, S. F. J. Organomet. Chem. 2006, 71, 4810
[27] Huang, K.-L.; Guo, C.; Cheng, L.-J.; Xie, L.-G.; Zhou, Q.-L.; Xu, X.-H.; Zhu, S.-F. Adv. Synth. Catal. 2013, 355, 2833.
[28] Shukla, P.; Sharma, A.; Pallavi, B.; Cheng, C.-H. Tetrahedron 2015, 71, 2260.
[29] Tenaglia, A.; Marc, S. J. Org. Chem. 2008, 73, 1397.
[30] Tenaglia, A.; Marc, S.; Giordano, L.; Riggi, I. D. Angew. Chem., Int. Ed. 2011, 50, 9062.
[31] Fan, B.-M.; Li, S.-F.; Chen, H.-L.; Lu, Z.-W.; Liu, S.-S.; Yang, Q.-J.; Yu, L.; Xu, J.-B.; Zhou, Y.-Y.; Wang, J. Adv. Synth. Catal. 2013, 355, 2827.
[32] Mo, D.-L.; Chen, B.; Ding, C.-H.; Dai, L.-X.; Ge, G.-C.; Hou, X.-L. Organometallics 2013, 32, 4465.
[33] Liu, S.-S.; Li, S.-F.; Chen, H.-L.; Yang, Q.-J.; Xu, J.-B.; Zhou, Y.-Y.; Yuan, M.-L.; Zeng, W.-M.; Fan, B.-M. Adv. Synth. Catal. 2014, 356, 2960.
[34] Mannathana, S.; Cheng, C.-H. Adv. Synth. Catal. 2014, 356, 2239.
[35] Zhou, Y.-Y.; Liu, S.-S.; Chen, H.-L.; Chen, J.-C.; Sun, W.-Q.; Li, S.-F.; Yang, Q.-J.; Fan, B.-M. Chin. J. Chem. 2015, 11, 15.
[36] Chen, J.-C.; Liu, S.-S.; Zhou, Y.-Y.; Li, S.-F.; Lin, C.-Y.; Bian, Z.-X.; Fan, B.-M. Organometallics 2015, 34, 4318.
[37] Menard, F.; Lautens, M. Angew. Chem., Int. Ed. 2008, 47, 2085.
[38] Zhang, T.-K.; Mo, D.-L.; Dai, L.-X.; Hou, X.-L. Org. Lett. 2008, 10, 3689.
[39] Machin, B.; Ballantine, M.; Mandel, J.; Blanchard, N.; Tam, W. J. Org. Chem. 2009, 74, 7261.
[40] Huang, X.-J.; Mo, D.-L.; Ding, C.-H.; Hou, X.-L. Synlett 2011, 943.
[41] Tsui, G. C.; Tsoung, J.; Dougan, P.; Lautens, M. Org. Lett. 2012, 14, 5542.
[42] Pan, X.-J.; Huang, G.-B.; Long, Y.-H.; Zuo, X.-J.; Xu, X.; Gu, F.-L.; Yang, D.-Q. J. Org. Chem. 2014, 45, 187.
[43] Zeng, Z.-Y.; Yang, D.-Q.; Long, Y.-H.; Pan, X.-J.; Huang, G.-B.; Zuo, X.-J.; Zhou, W. J. Org. Chem. 2014, 79, 5249.
[44] Edmundsa, M.; Menarda, M. L.; Tam, W. Synth. Commun. 2015, 45, 468.
[45] Arrayas, R. G.; Cabrera, S.; Carretero, J. C. Org. Lett. 2005, 7, 219.
[46] Arrayas, R. G.; Cabrera, S.; Carretero, J. C. Synthesis 2006, 1205.
[47] Zhu, S.-F.; Yang, Y.; Wang, L.-X.; Liu, B.; Zhou, Q.-L. Org. Lett. 2005, 7, 2333.
[48] Zhang, W.; Zhu, S.-F.; Qiao, X.-C.; Zhou, Q.-L. Chem. Asian J. 2008, 3, 2105.
[49] Millet, R.; Bernardez, T.; Palais, L.; Alexakis, A. Synthesis 2009, 2101.
[50] Yang, D.-Q.; Liang, N. Org. Biomol. Chem. 2014, 10, 1039.
[51] Pineschi, M.; Moro, F. D.; Crotti, P.; Macchia, F. Org. Lett. 2005, 7, 3605.
[52] Millet, R.; Bernardez, T.; Palais, L.; Alexakis, A. Tetrahedron Lett. 2009, 50, 3474.
[53] Wu, M.-S.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004, 69, 8407.
[54] Wu, M.-S.; Jeganmohan, M.; Cheng, C.-H. J. Org. Chem. 2005, 70, 9545.
[55] Nájera, C.; Yus, M. Curr. Org. Chem. 2003, 7, 867.
[56] Rappoport, Z.; Marek, I. The Chemistry of Organolithium Compounds, John Wiley & Sons Ltd, Chichester, UK, 2004, Chapter 1.
[57] Bos, P. H.; Rudolph, A.; Perez, M.; Fananas, M.; Harutyunyan, S. R.; Feringa, B. L. Chem. Commun 2012, 48, 1748.
[58] Sawama, Y.; Sawama, Y.; Krause, N. Org. Lett. 2009, 11, 5034.
[59] Sawama, Y.; Kawamoto, K.; Satake, H.; Krause, N.; Kita, Y. Synlett 2010, 2151.
[60] Loh, C.; Fang, X.; Peters, B.; Lautens, M. Chem. Eur. J. 2015, 21, 13883.
[61] Zhou, H.; Li, J.; Yang, H.; Xia, C.; Jiang, G. Org. Lett. 2015, 17, 4628.

Outlines

/