研究专题

重氮化合物参与的不对称催化多组分反应

  • 唐敏 ,
  • 邢栋 ,
  • 蔡茂强 ,
  • 胡文浩
展开
  • a 华东师范大学上海分子治疗与新药创制工程技术研究中心 上海 200062;
    b 华东师范大学化学系 上海 200062

收稿日期: 2014-04-03

  修回日期: 2014-05-21

  网络出版日期: 2014-06-09

基金资助

国家自然科学基金(Nos.21125209,21332003)、科技部杰出青年基金(No.2011CB808600)和上海市科委重点基础研究基金(No.12JC1403800)资助项目.

Diazo Compounds-Involved Catalytic Asymmetric Multicomponent Reactions

  • Tang Min ,
  • Xing Dong ,
  • Cai Maoqiang ,
  • Hu Wenhao
Expand
  • a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062;
    b Department of Chemistry, East China Normal University, Shanghai 200062

Received date: 2014-04-03

  Revised date: 2014-05-21

  Online published: 2014-06-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21125209, 21332003), the Ministry of Science and Technology of China (No. 2011CB808600) and the Science and Technology Commission of Shanghai Municipality (No. 12JC1403800).

摘要

综述了近年来我们研究小组在重氮化合物参与的不对称催化多组分反应方面的研究进展. 基于对重氮化合物经由金属卡宾而生成的羟基叶立德、氨基叶立德或活泼离子对中间体的亲电捕捉,以及不同模式的协同催化策略,发展了不同类型的不对称催化多组分反应,实现了多种高效构建多官能团手性化合物的合成策略.

本文引用格式

唐敏 , 邢栋 , 蔡茂强 , 胡文浩 . 重氮化合物参与的不对称催化多组分反应[J]. 有机化学, 2014 , 34(7) : 1268 -1276 . DOI: 10.6023/cjoc201404010

Abstract

This accounts covers the recent advances in diazo compounds-involved catalytic asymmetric multicomponent reactions developed by our research group. Based on the electrophilic trapping of active oxonium ylides, ammonium ylides or zwitterionic intermediates that generated from diazo compounds via metal carbenes, an array of catalytic asymmetric multicomponent reactions have been developed. Cooperative catalytic strategies have been applied to control enantioselectivity of the reactions. These transformations offer efficient and powerful strategies for the synthesis of polyfunctional chiral molecules

参考文献

[1] (a) Zhu, J.; Bienaymé, H. Multicomponent Reactions, Wiley, Weinheim, Germany, 2005.

(b) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602.

(c) Dömling, A. Chem. Rev. 2006, 106, 17.

(d) Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.

[2] (a) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.

(b) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.

(c) Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937.

(d) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.

(e) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365.

(f) Li, Y.; Huang, C.; Xu, P.; Zhang, Y.; Wang, J. Acta Chim. Sinica 2012, 70, 2024 (in Chinese).

(李玉叶, 黄重行, 许鹏飞, 张艳, 王剑波, 化学学报, 2012, 70, 2024.)

[3] Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427.

[4] Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.

[5] Staffan, T.; Peter, S. Adv. Synth. Catal. 2006, 348, 2421.

[6] Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 933.

[7] Wang, Y.; Zhu, Y.; Chen, Z.; Mi, A.; Hu, W.; Doyle, M. P. Org. Lett. 2003, 5, 3923.

[8] (a) Wang, Y.; Chen, Z.; Mi, A.; Hu, W. Chem. Commun. 2004, 2486.

(b) Guo, X.; Yue, Y.; Hu, G.; Zhou, J.; Zhao, Y.; Yang, L.; Hu, W. Synlett 2009, 2109.

(c) Zhu, Y.; Zhai, C.; Yang, L.; Hu, W. Eur. J. Org. Chem. 2011, 1113.

(d) Zhang, X.; Ji, J.; Zhu, Y.; Jing, C.; Li, M.; Hu, W. Org. Biomol. Chem. 2012, 10, 2133.

[9] (a) Lu, C.; Liu, H.; Chen, Z.; Hu, W.; Mi, A. Org. Lett. 2005, 7, 83.

(b) Han, X.; Jiang, L.; Tang, M.; Hu, W. Org. Biomol. Chem. 2011, 9, 3839.

(c) Guo, X.; Huang, H.; Yang, L.; Hu, W. Org. Lett. 2007, 9, 4721.

(d) Huang, H.; Guo, X.; Hu, W. Angew. Chem., Int. Ed. 2007, 46, 1337.

[10] Hu, W. H.; Xu, X. F.; Zhou, J.; Liu, W. J.; Huang, H. X.; Hu, J.; Yang, L. P.; Gong, L. Z. J. Am. Chem. Soc. 2008, 130, 7782.

[11] Xu, X.; Zhou, J.; Yang, L.; Hu, W. Chem. Commun. 2008, 6564.

[12] Qian, Y.; Jing, C.; Shi, T.; Ji, J.; Tang, M.; Zhou, J.; Zhai, C.; Hu, W. ChemCatChem 2011, 3, 653.

[13] Qian, Y.; Jing, C.; Liu, S.; Hu, W. Chem. Commun. 2013, 49, 2700.

[14] Qian, Y.; Xu, X.; Jiang, L.; Prajapati, D.; Hu, W. J. Org. Chem. 2010, 75, 7483.

[15] Xu, X.; Qian, Y.; Yang, L.; Hu, W. Chem. Commun. 2011, 47, 797.

[16] Zhang, X.; Huang, H.; Guo, X.; Guan, X.; Yang, L.; Hu, W. Angew. Chem., Int. Ed. 2008, 47, 6647.

[17] Guan, X.; Yang, L.; Hu, W. Angew. Chem., Int. Ed. 2010, 49, 2190.

[18] Jiang, J.; Xu, H.; Xi, J.; Ren, B.; Lv, F.; Guo, X.; Jiang, L.; Zhang, Z.; Hu, W. J. Am. Chem. Soc. 2011, 133, 8428.

[19] Jiang, J.; Ma, X.; Liu, S.; Qian, Y.; Lv, F.; Qiu, L.; Wu, X.; Hu, W. Chem. Commun. 2013, 49, 4238.

[20] Jing, C.; Xing, D.; Qian, Y.; Hu, W. Synthesis 2014, 46, 1348.

[21] Ren, L.; Lian, X.; Gong, L. Chem. Eur. J. 2013, 19, 3315.

[22] Zhou, C.; Wang, J.; Wei, J.; Xu, Z.; Guo, Z.; Low, K.; Che, C. Angew. Chem., Int. Ed. 2012, 51,11376.

[23] Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nat. Chem 2012, 4, 733.

[24] Qiu, H.; Zhang, D.; Liu, S.; Qiu, L.; Zhou, J.; Qian, Y.; Zhai, C.; Hu, W. Acta Chim. Sinica 2012, 70, 2484 (in Chinese).

(邱晃, 张丹, 刘顺英, 邱林, 周俊, 钱宇, 翟昌伟, 胡文浩, 化学学报, 2012, 70, 2484.)

[25] Maryanoff, B. E. J. Org. Chem. 1979, 44, 4410.

[26] Zhang, D.; Qiu, H.; Jiang, L.; Lv, F.; Ma, C.; Hu, W. Angew. Chem., Int. Ed. 2013, 52, 13356.

文章导航

/