Diazo Compounds-Involved Catalytic Asymmetric Multicomponent Reactions

doi:10.6023/cjoc201404010

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1268-1276.DOI: 10.6023/cjoc201404010 Previous Articles Next Articles

ACCOUNT

重氮化合物参与的不对称催化多组分反应

唐敏^a,b, 邢栋^a,b, 蔡茂强^a,b, 胡文浩^a,b

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 发布日期:2014-06-09
通讯作者: 胡文浩 E-mail:whu@chem.ecnu.edu.cn
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^a,b, Xing Dong^a,b, Cai Maoqiang^a,b, Hu Wenhao^a,b

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:2014-04-03 Revised:2014-05-21 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).

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

Key words: diazo compound, metal carbene, catalytic asymmetric, multicomponent reaction, cooperative catalysis

Cite this article

Tang Min, Xing Dong, Cai Maoqiang, Hu Wenhao. Diazo Compounds-Involved Catalytic Asymmetric Multicomponent Reactions[J]. Chin. J. Org. Chem., 2014, 34(7): 1268-1276.

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[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.

重氮化合物参与的不对称催化多组分反应

Diazo Compounds-Involved Catalytic Asymmetric Multicomponent Reactions

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