Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF3 Group from 2,2,2-Trifluoroacetophenone Substrates

doi:10.6023/cjoc201612006

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 936-942.DOI: 10.6023/cjoc201612006 Previous Articles Next Articles

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手性硫脲催化的不对称Henry反应:以2,2,2-三氟甲基苯乙酮作为底物构筑含有CF₃的手性中心

吴丽丽, 苏瀛鹏, 种思颖, 张为钢, 黄丹凤, 王克虎, 胡雨来

西北师范大学化学化工学院兰州 730070

收稿日期:2016-12-02 修回日期:2017-01-04 发布日期:2017-01-10
通讯作者: 苏瀛鹏, 胡雨来 E-mail:suyp51@nwnu.edu.cn;huyl@nwnu.edu.cn
基金资助:
国家自然科学基金（Nos.21362033，21262031）资助项目.

Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates

Wu Lili, Su Yingpeng, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai

a. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2016-12-02 Revised:2017-01-04 Published:2017-01-10
Contact: 10.6023/cjoc201612006 E-mail:suyp51@nwnu.edu.cn;huyl@nwnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21362033, 21262031).

1. Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates.PDF(2082KB)

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Wu Lili, Su Yingpeng, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates[J]. Chin. J. Org. Chem., 2017, 37(4): 936-942.

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[1] (a) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
(b) Ni, C. F.; Zhu, L. G.; Hu, J. B. Acta Chim. Sinica 2015, 73, 90 (in Chinese).
(倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
(c) Xu, J. B.; Chen, P. H.; Ye, J. X.; Liu, G. S. Acta Chim. Sinica 2015, 73, 1294 (in Chinese).
(徐佳斌, 陈品红, 叶金星, 刘国生, 化学学报, 2015, 73, 1294.)
[2] (a) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2nd ed., Wiley-VCH, Weinheim, Germany, 2013, pp. 299~301.
(b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(c) Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine, John Wiley & Sons Inc., Hoboken, New Jersey 2008, pp. 1~351.
(d) Hagmann, W. J. Med. Chem. 2008, 51, 4359.
(e) Filler, R.; Saha, R. Future Med. Chem. 2009, 1, 777.
(f) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley, Chichester, U. K., 2009, pp. 1~523.
(g) Lin, G.-Q.; You, Q.-D.; Cheng, J.-F. Chiral Drugs: Chemistry and Biological Action, Wiley, Hoboken, New Jersey, 2011.
(h) Purser, S.; Moore, P.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(i) Schäcke, H.; Schottelius, A.; Döcke, W.-D.; Strehlke, P.; Jaroch, S.; Schmees, N.; Rehwinkel, H.; Hennekes, H.; Asadullah, K. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 227.
(j) Gauthier, J.; Chauret, N.; Cromlish, W.; Desmarais, S.; Duong, L.; Falgueyret, J.-P.; Kimmel, D.; Lamontagne, S.; Léger, S.; LeRiche, T.; Li, C.; Massé, F.; McKay, D.; Nicoll-Griffith, D.; Oballa, R.; Palmer, J.; Percival, M.; Riendeau, D.; Robichaud, J.; Rodan, G.; Rodan, S.; Seto, C.; Thérien, M.; Truong, V.-L.; Venuti, M.; Wesolowski, G.; Young, R.; Zamboni, R.; Black, W. Bioorg. Med. Chem. Lett. 2008, 18, 923.
(k) O'Shea, P.; Chen, C.-Y.; Gauvreau, D.; Gosselin, F.; Hughes, G.; Nadeau, C.; Volante, R. J. Org. Chem. 2009, 74, 1605.
(l) Ojima, I.; Slater, J. Chirality 1997, 9, 487.
(m) Pierce, M.; Parsons, R.; Radesca, L.; Lo, Y.; Silverman, S.; Moore, J.; Islam, Q.; Choudhury, A.; Fortunak, J.; Nguyen, D.; Luo, C.; Morgan, S.; Davis, W.; Confalone, P.; Chen, C.-Y.; Tillyer, R.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A.; Corley, E.; Grabowski, E.; Reamer, R.; Reider, P. J. Org. Chem. 1998, 63, 8536.
(n) Corbett, J.; Ko, S.; Rodgers, J.; Gearhart, L.; Magnus, N.; Bacheler, L.; Diamond, S.; Jeffrey, S.; Klabe, R.; Cordova, B.; Garber, S.; Logue, K.; Trainor, G.; Anderson, P.; Erickson-Viitanen, S. J. Med. Chem. 2000, 43, 2019.
(o) Zhang, K.; Xu, X. H.; Qing, F. L. Chin. J. Org. Chem. 2015, 35, 556 (in Chinese).
(张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)
(p) Ni, Y.; Xu, T. M.; Zhong, L. K.; Kong, X. Y.; Shi, J.-J.; Liu, X. H.; Kong, X. L.; Ji, W. J.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 2218 (in Chinese).
(倪芸, 许天明, 钟良坤, 孔晓燕, 史建俊, 刘幸海, 孔小林, 姬文娟, 谭成侠, 有机化学, 2015, 35, 2218.)
(q) Dai, H.; Li, H.; Jin, Z. C.; Liu, W. Y.; Xiao, Y.; He, H. B.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 185 (in Chinese).
(戴红, 李宏, 金智超, 刘文永, 肖瑶, 何海兵, 汪清民, 石玉军, 有机化学, 2016, 36, 185.)
[3] (a) Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633.
(b) Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1.
(c) Zheng, Y.; Ma, J.-A. Adv. Synth. Catal. 2010, 352, 2745.
(d) Valero, G.; Companyó, X.; Rios, R. Chem.-Eur. J. 2011, 17, 2018.
(e) Genoni, A.; Benaglia, M.; Massolo, E.; Rossi, S. Chem. Commun. 2013, 49, 8365.
[4] Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
[5] (a) Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron: Asymmetry 2006, 17, 3315.
(b) Marcelli, T.; van der Haas, R.; van Maarseveen, J.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929.
(c) Hammar, P.; Marcelli, T.; Hiemstra, H.; Himo, F. Adv. Synth. Catal. 2007, 349, 2537.
[6] (a) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599.
(b) Tur, F.; Saá, J. Org. Lett. 2007, 9, 5079.
(c) Saá, J. M.; Tur, F.; González, J. Chirality 2009, 21, 836.
(d) Tur, F.; Mansilla, J.; Lillo, V. J.; Saá, J. M. Synthesis 2010, 1909.
(e) Vlatkovic, M.; Bernardi, L.; Otten, E.; Feringa, B. L. Chem. Commun. 2014, 50, 7773.
(f) Das, A.; Choudhary, M. K.; Kureshy, R. I.; Jana, K.; Verma, S.; Khan, N. H.; Abdi, S. H. R.; Bajaj, H. C.; Ganguly, B., Tetrahedron 2015, 71, 5229.
[7] Bandini, M.; Sinisi, R.; Umani-Ronchi, A. Chem. Commun. 2008, 4360.
[8] Palacio, C.; Connon, S. J. Org. Lett. 2011, 13, 1298.
[9] (a) Doyle, A.; Jacobsen, E. Chem. Rev. 2007, 107, 5713.
(b) Connon, S. Chem. Commun. 2008, 2499.
(c) Hideto, M.; Yoshiji, T. Chem. Soc. Jpn. 2008, 81, 785.
(d) Yu, X.; Wang, W. Chem.-Asian J. 2008, 3, 516.
(e) Schreiner, P. Chem. Soc. Rev. 2003, 32, 289.
[10] (a) Xu, J.; Hu, Y.; Huang, D.; Wang, K.-H.; Xu, C.; Niu, T. Adv. Synth. Catal. 2012, 354, 515.
(b) Ji, S.; Alkhalil, A.; Su, Y.; Xia, X.; Chong, S.; Wang, K.-H.; Huang, D.; Fu, Y.; Hu, Y. Synlett 2015, 26, 1725.
[11] (a) Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Org. Lett. 2005, 7, 1967.
(b) Bassas, O.; Huuskonen, J.; Rissanen, K.; Koskinen, A. M. P. Eur. J. Org. Chem. 2009, 1340.
[12] (a) Rudzinski, D.; Kelly, C.; Leadbeater, N. Chem. Commun. 2012, 48, 9610.
(b) Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G.; Olah, G. Angew. Chem., Int. Ed. 1998, 37, 820.
[13] Liu, W.; Lai, X.; Zha, G.; Xu, Y.; Sun, P.; Xia, T.; Shen, Y. Org. Biomol. Chem. 2016, 14, 3603.
[14] Lu, L.; Jerome, C. WO 2014114250, 2014 [Chem. Abstr. 2014, 161, 290900].

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手性硫脲催化的不对称Henry反应:以2,2,2-三氟甲基苯乙酮作为底物构筑含有CF₃的手性中心

Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates

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手性硫脲催化的不对称Henry反应:以2,2,2-三氟甲基苯乙酮作为底物构筑含有CF3的手性中心