综述与进展

过渡金属催化氧(氮)杂二环烯烃与碳负离子型亲核试剂的不对称开环反应研究进展

  • 仵瑞华 ,
  • 杨文 ,
  • 程果 ,
  • 李玥 ,
  • 杨定乔
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  • 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006

收稿日期: 2016-04-03

  修回日期: 2016-05-17

  网络出版日期: 2016-06-02

基金资助

国家自然科学基金(Nos.21172081,21372090)、广东省自然科学基金重点(No.S2013020013091)和广州市科技计划(No.156300018)资助项目.

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
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  • 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).

摘要

综述了近年来过渡金属催化氧(氮)杂二环烯烃与碳负离子型亲核试剂的不对称开环反应研究进展,重点讨论了过渡金属催化剂的种类、碳负离子型亲核试剂的类型、配体、底物结构、溶剂和添加剂等因素对不对称开环反应的影响,并对部分不对称开环反应的可能机理进行了讨论.

本文引用格式

仵瑞华 , 杨文 , 程果 , 李玥 , 杨定乔 . 过渡金属催化氧(氮)杂二环烯烃与碳负离子型亲核试剂的不对称开环反应研究进展[J]. 有机化学, 2016 , 36(10) : 2368 -2379 . DOI: 10.6023/cjoc201604006

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.

参考文献

[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.

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