Cascade Halo-Michael/Aldol Reaction and Its Application in Synthesis

doi:10.6023/cjoc201803005

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1608-1625.DOI: 10.6023/cjoc201803005 Previous Articles Next Articles

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Halo-Michael/Aldol串联反应及其在合成中的应用

代义华^a, 申艳芳^a, 高栓虎^a,b

a 华东师范大学化学与分子工程学院上海绿色化学与化工工程绿色化重点实验室上海 200062;
b 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

收稿日期:2018-03-04 修回日期:2018-04-02 发布日期:2018-04-04
通讯作者: 高栓虎 E-mail:shgao@chem.ecnu.edu.cn
基金资助:
国家自然科学基金（No.21772044）、上海市优秀学术带头人计划（No.18XD1401500）、青年拔尖人才项目及中央高校基本科研业务费.

Cascade Halo-Michael/Aldol Reaction and Its Application in Synthesis

Dai Yihua^a, Shen Yanfang^a, Gao Shuanhu^a,b

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062

Received:2018-03-04 Revised:2018-04-02 Published:2018-04-04
Contact: 10.6023/cjoc201803005 E-mail:shgao@chem.ecnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21772044), the Program of Shanghai Academic/Technology Research Leader (No. 18XD1401500), the National Young Top-Notch Talent Support Program and the Fundamental Research Funds for the Central Universities.

Michael addition and aldol reaction are among the most basic and commoly used reactions. Cascade halo-Michael/Aldol reaction can effectively improve the atomic economy and step economy of organic synthesis. After the Michael addition of α,β-unsaturated compound with halide ion (Cl^-, Br^-, I^-), the reactive intermediate reacts with aldehyde through aldol reaction in the same reaction system. This process is called cascade halo-Michael/Aldol reaction. The cascade halo-Michael/Aldol reaction and its applications in the synthesis of related compounds according to the types of Lewis acid are introduced.

Key words: halo-michael/aldol reaction, cascade reaction, Lewis acid, application, synthesis

Cite this article

Dai Yihua, Shen Yanfang, Gao Shuanhu. Cascade Halo-Michael/Aldol Reaction and Its Application in Synthesis[J]. Chin. J. Org. Chem., 2018, 38(7): 1608-1625.

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[1] Komnenos, T. Justus Liebigs Ann. Chem. 1883, 218, 145.
[2] Michael, A. J. Prakt. Chem. 1887, 35, 349.
[3] Michael, A. J. Prakt. Chem. 1894, 49, 20.
[4] Claisen, L. J. Prakt. Chem. 1887, 35, 413.
[5] Tokoroyama, T. Eur. J. Org. Chem. 2010, 2010, 2009.
[6] Mukaiyama, T. Org. React. 2005, 28, 203.
[7] Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
[8] Heathcock, C. H. Compr. Org. Synth. 1991, 2, 133.
[9] Schetter, B.; Mahrwald, R. Angew. Chem., Int. Ed. Engl. 2006, 45, 7506.
[10] Kan, S. B.; Ng, K. K.; Paterson, I. Angew. Chem., Int. Ed. Engl. 2013, 52, 9097.
[11] Acheson, R. M.; Robinson, R. J. Chem. Soc. 1952, 1127.
[12] Heathcock, C. H.; Ellis, J. E.; McMurry, J. E.; Coppolino, A. Tetrahedron Lett. 1971, 12, 4995.
[13] Rapson, W. S.; Robinson, R. J. Chem. Soc. 1935, 1285.
[14] Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659.
[15] Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005.
[16] Ciganek, E. Org. React. 2004, 51, 201.
[17] Masson, G.; Housseman, C.; Zhu, J. Angew. Chem., Int. Ed. Engl. 2007, 46, 4614.
[18] Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1.
[19] Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
[20] Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.
[21] Basavaiah, D.; Veeraraghavaiah, G. Chem. Soc. Rev. 2012, 41, 68.
[22] Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 27, 4767.
[23] Shi, M.; Jiang, J.-K. Tetrahedron 2000, 56, 4793.
[24] Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397.
[25] Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66, 406.
[26] Han, Z.; Uehira, S.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 7854.
[27] Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-I. Angew. Chem., Int. Ed. 2000, 39, 2358.
[28] Medvedeva, A. S.; Demina, M. M.; Novopashin, P. S.; Sarapulova, G. I.; Afonin, A. V. Mendeleev Commun. 2002, 12, 110.
[29] Li, G.; Wei, H.-X.; Gao, J. J.; Johnson, J. Synth. Commun. 2002, 32, 1765.
[30] Wei, H.-X.; Gao, J. J.; Li, G. Tetrahedron Lett. 2001, 42, 9119.
[31] Wei, H.-X.; Kim, S. H.; Caputo, T. D.; Purkiss, D. W.; Li, G. Tetrahedron 2000, 56, 2397.
[32] Shi, M.; Wang, C.-J. Tetrahedron 2002, 58, 9063.
[33] Shi, M.; Wang, C.-J. Helv. Chim. Acta 2002, 85, 841.
[34] Hachiya, I.; Ito, S.; Kayaki, S.; Shimizu, M. Asian J. Org. Chem. 2013, 2, 931.
[35] Yashiro, K.; Ito, S.; Kayaki, S.; Sakata, K.; Mizota, I.; Hachiya, I.; Shimizu, M. Tetrahedron 2016, 72, 6875.
[36] Yagi, K.; Turitani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2002, 4, 3111.
[37] Ciesielski, J.; Canterbury, D. P.; Frontier, A. J. Org. Lett. 2009, 11, 4374.
[38] Deng, G.-H.; Hu, H.; Wei, H.-X.; Paré, P. W. Helv. Chim. Acta 2003, 86, 3510.
[39] Wei, H.-X.; Hu, J.; Jasoni, R. L.; Li, G.; Paré, P. W. Helv. Chim. Acta 2004, 87, 2359.
[40] Wei, H.-X.; Hu, J.; Purkiss, D. W.; Paré, P. W. Tetrahedron Lett. 2003, 44, 949.
[41] Wei, H.-X.; Jasoni, R. L.; Hu, J.; Li, G.; Paré, P. W. Tetrahedron 2004, 60, 10233.
[42] Bugarin, A.; Connell, B. T. Tetrahedron Lett. 2015, 56, 3285.
[43] (a) Wei, H. X.; Timmons, C.; Farag, M. A.; Paré, P. W.; Li, G. Org. Biomol. Chem. 2004, 2, 2893.
(b) Wei, H.-X.; Gao J. J.; Li G.; Paré, P. W. Tetrahedron Lett. 2002, 43, 5677.
[44] Ciesielski, J.; Cariou, K.; Frontier, A. J. Org. Lett. 2012, 14, 4082.
[45] Ciesielski, J.; Gandon, V.; Frontier, A. J. J. Org. Chem. 2013, 78, 9541.
[46] Wei, H.-X.; Kim, S. H.; Li, G. Org. Lett. 2002, 4, 3691.
[47] Lee, S. I.; Hwang, G. S.; Shin, S. C.; Lee, T. G.; Jo, R. H.; Ryu, D. H. Org. Lett. 2007, 9, 5087.
[48] Ciesielski, J.; Leboeuf, D.; Stern, H. A.; Frontier, A. J. Adv. Synth. Catal. 2013, 355, 2077.
[49] Ryu, D.; Hwang, G.-S.; Lee, S. Synlett 2007, 0059.
[50] Zhang, C.; Lu, X. Synthesis 1996, 586.
[51] Yadav, J. S.; Reddy, B. V. S.; Gupta, M. K.; Pandey, S. K. J. Mol. Catal. A:Chem. 2007, 264, 309.
[52] Yadav, J.; Reddy, B.; Gupta, M.; Eeshwaraiah, B. Synthesis 2004, 57.
[53] Xu, X.; Chen, D.; Wei, H. X.; Li, G.; Xiao, T. L.; Armstrong, D. W. Chirality 2003, 15, 139.
[54] Wei, H.-X.; Chen, D.; Xu, X.; Li, G.; Paré, P. W. Tetrahedron:Asymmetry 2003, 14, 971.
[55] Li, G.; Xu, X.; Chen, D.; Timmons, C.; Carducci, M. D.; Headley, A. D. Org. Lett. 2003, 5, 329.
[56] Chen, D.; Guo, L.; Kotti, S. R. S. S.; Li, G. Tetrahedron:Asymmetry 2005, 16, 1757.
[57] Chen, D.; Timmons, C.; Liu, J.; Headley, A.; Li, G. Eur. J. Org. Chem. 2004, 2004, 3330.
[58] Lee, S. I.; Jang, J. H.; Hwang, G. S.; Ryu, D. H. J. Org. Chem. 2013, 78, 770.
[59] Senapati, B. K.; Hwang, G. S.; Lee, S.; Ryu, D. H. Angew. Chem., Int. Ed. Engl. 2009, 48, 4398.
[60] Sharma, V.; McLaughlin, M. L. J. Comb. Chem. 2010, 12, 327.
[61] Jeon, K. J.; Lee, K.-J. J. Heterocycl. Chem. 2008, 45, 615.
[62] Lee, K.-J.; Lim, H.; Ji, S.-H. Synthesis 2007, 2454.
[63] Ribaucourt, A.; Hodgson, D. M. Org. Lett. 2016, 18, 4364.
[64] Ranatunga, S.; Kim, J. S.; Pal, U.; Del Valle, J. R. J. Org. Chem. 2011, 76, 8962.
[65] Ahmed, N.; Ali, H.; van Lier, J. E. J. Porphyrins Phthalocyanines 2006, 10, 1172.
[66] Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Chem.-Eur. J. 2007, 13, 1610.
[67] Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Org. Lett. 2006, 8, 5267.
[68] Sloman, D. L.; Bacon, J. W.; Porco, J. A. Jr. J. Am. Chem. Soc. 2011, 133, 9952.
[69] Sloman, D. L.; Mitasev, B.; Scully, S. S.; Beutler, J. A.; Porco, J. A. Jr. Angew. Chem., Int. Ed. Engl. 2011, 50, 2511.
[70] Winter, D. K.; Endoma-Arias, M. A.; Hudlicky, T.; Beutler, J. A.; Porco, J. A. Jr. J. Org. Chem. 2013, 78, 7617.
[71] Butler, J. R.; Wang, C.; Bian, J.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 9956.
[72] Rujirawanich, J.; Kim, S.; Ma, A. J.; Butler, J. R.; Wang, Y.; Wang, C.; Rosen, M.; Posner, B.; Nijhawan, D.; Ready, J. M. J. Am. Chem. Soc. 2016, 138, 10561.
[73] Sugano, M.; Sato, A.; Iijima, Y.; Furuya, K.; Haruyama, H.; Yoda, K.; Hata, T. J. Org. Chem. 1994, 59, 564.
[74] Sugano, M.; Sato, A.; Iijima, Y.; Furuya, K.; Kuwano, H.; Hata, T. J. Antibiot. 1995, 48, 1188.
[75] Sugano, M.; Sato, A.; Iijima, Y.; Oshima, T.; Furuya, K.; Kuwano, H.; Hata, T.; Hanzawa, H. J. Am. Chem. Soc. 1991, 113, 5463.
[76] Chu, M.; Patel, M. G.; Gullo, V. P.; Truumees, I.; Puar, M. S.; McPhail, A. T. J. Org. Chem. 1992, 57, 5817.

Halo-Michael/Aldol串联反应及其在合成中的应用

Cascade Halo-Michael/Aldol Reaction and Its Application in Synthesis

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