综述与进展

有机小分子不对称催化Michael加成的研究进展

  • 应安国 ,
  • 武承林 ,
  • 付永前 ,
  • 任世斌 ,
  • 梁华定
展开
  • 台州学院医药化工学院 台州 318000

收稿日期: 2012-03-26

  修回日期: 2012-05-11

  网络出版日期: 2012-05-05

基金资助

国家自然科学基金(No.21106090)、中国博士后基金面上(No.2012M511352)资助项目

Progress in the Application of Organocatalysis to Asymmetric Michael Additions

  • Ying ,
  • Anguo ,
  • Wu Chenglin ,
  • Fu Yongqian ,
  • Ren Shibin
Expand
  • School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000

Received date: 2012-03-26

  Revised date: 2012-05-11

  Online published: 2012-05-05

Supported by

Project supported by the National Natural Science Foundation of China (No.21106090) and the Postdoctoral Foundation of China (No.2012M511352)

摘要

有机小分子催化成为现在最热门的研究领域之一.不对称Michael加成反应是合成具有一个或多个手性中心合成砌块和药物中间体的重要方法.介绍了近3年来有机小分子伯胺衍生物、吡咯烷衍生物、(硫)脲、手性方酰胺和磷酸等在不对称催化Michael加成中的应用研究进展.对各种小分子结构和催化活性的关系、催化剂诱导活化机理以及各种催化体系在药物和关键中间体合成中的应用也进行详细的评述.

本文引用格式

应安国 , 武承林 , 付永前 , 任世斌 , 梁华定 . 有机小分子不对称催化Michael加成的研究进展[J]. 有机化学, 2012 , 32(9) : 1587 -1604 . DOI: 10.6023/cjoc201203009

Abstract

Organocatalysis has become one of the most intensively research fields. Asymmetric Michael addition is a key method for synthesis of versatile synthetic buildings and pharmaceutical intermediates, which include one or more stereo-chemical centers. The organocatalysts reported over the past three years for the asymmetric Michael addition are reviewed including primary amine, pyrrolidine based derivatives, (thio) urea, chiral squaramides and phosphoric acids. The relationship between structure of organocatalysts and their catalytic activities, catalytic reaction mechanism and the applications of these protocols for the preparation of drugs and bioactive intermediates are also introduced.

参考文献

[1] Kazmaier, U. Angew. Chem., Int. Ed. 2009, 48, 5790.

[2] Trost, B. M. J. Am. Chem. Soc. 2009, 131, 4572.

[3] Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.

[4] Pellissier, H. Tetrahedron 2007, 63, 9267.   

[5] Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638.

[6] Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.   

[7] Vicario, J. L.; Badia, D.; Carrillo, L. Synthesis 2007, 2065.

[8] Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.

[9] Li, N.; Xi, G.-H.; Wu, Q.-H.; Liu, W.-H.; Ma, J.-J.; Wang, C. Chin. J. Org. Chem. 2009, 29, 1018 (in Chinese). (李宁, 郗国宏, 吴秋华, 刘伟华, 马晶军, 王春, 有机化学, 2009, 29, 1018.)

[10] Krishna, P. R.; Sreeshailam, A.; Srinivas, R. Tetrahedron 2009, 65, 9657.   

[11] Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.

[12] List, B. Chem. Commun. 2006, 42, 819.

[13] Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638.

[14] Huge, D. J. In New Comprehensive Biochemistry, Vol. 6, Ed.: Page, M. I., Elsevier, Amsterdam, 1984, pp. 271~301.   

[15] Chen, Y.-C. Synlett 2008, 1919.   

[16] Wang, J.-F.; Wang, X.; Ge, Z.-M.; Cheng, T.-M.; Li, R.-T. Chem. Commun. 2010, 46, 1751.

[17] Alali, F. W.; Liu, Y. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 524.

[18] Dalpiaz, A.; Pavan, B.; Scaglianti, M.; Vitali, F.; Bortolotti, F.; Biondi, C.; Scatturin, A.; Manfredini, S. Int. J. Pharm. 2005, 291, 171.

[19] Rao, Y. S. Chem. Rev. 1976, 76, 625.

[20] Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.

[21] Wang, J.-F.; Qi, C.; Ge, Z.-M.; Cheng, T.-M.; Li, R.-T. Chem. Commun. 2010, 46, 2124.

[22] Ballini, R.; Bosica, G.; Cioci, G.; Fiorini, D.; Petrini, M. Tetrahedron 2003, 59, 3603.   

[23] Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862.

[24] Yu, F.; Sun, X.-M.; Jin, Z.-C.; Wen, S.-G.; Liang, X.-M.; Ye, J.-X. Chem. Commun. 2010, 46, 4589.

[25] Peng, L.; Xu, X.-Y.; Wang, L.-L.; Huang, J.; Bai, J.-F.; Huang, Q.-C.; Wang, L.-X. Eur. J. Org. Chem. 2010, 1849.

[26] Chapsal, B. D.; Ojima, I. Org. Lett. 2006, 8, 1395.

[27] Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 10596.

[28] Nicolaou, K. C.; Dalby, S. M.; Majumder, U. J. Am. Chem. Soc. 2008, 130, 14942.

[29] Huang, H.-C.; Jin, Z.-C.; Zhu, K.-L.; Liang, X.-M.; Ye, J.-X. Angew. Chem., Int. Ed. 2011, 50, 3232.

[30] Huang, H.; Yu, F.; Jin, Z.; Li, W.; Wu, W.; Liang, X.; Ye, J. Chem. Commun. 2010, 46, 5957.

[31] Lu, A.-D.; Liu, T.; Wu, R.-H.; Wang, Y.-M.; Wu, G.-P.; Zhou, Z.-H.; Fang, J.-X.; Tang, C.-C. J. Org. Chem. 2011, 76, 3872.

[32] Sundberg, R. J. In The Chemistry of Indoles, Ed.: Blomquist, A. T., Academic Press, New York, 1970.   

[33] Laronze, M. Tetrahedron Lett. 2002, 43, 7925.   

[34] Hong, L.; Sun, W.-S.; Liu, C.-X.; Wang, L.; Wong, K.; Wang, R. Chem. Eur. J. 2009, 15, 11105.   

[35] Klunder, A. J. H.; Zhu, J.; Zwanenburg, B. Chem. Rev. 1999, 99, 1163.

[36] Miyashita, M.; Saino, M. Science 2004, 305, 495.   

[37] Goeke, A.; Mertl, D.; Brunner, G. Angew. Chem., Int. Ed. 2005, 44, 99.

[38] Yang, Y.-Q.; Chai, Z.; Wang, H.-F.; Chen, X.-K.; Cui, H.-F.; Zheng, C.-W.; Xiao, H.; Li, P.; Zhao, G. Chem. Eur. J. 2009, 15, 13295.   

[39] Mao, Z.-F.; Jia, Y.-M.; Li, W.-Y.; Wang, R. J. Org. Chem. 2010, 75, 7428.

[40] Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2006, 128, 734.

[41] Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331.

[42] Sil, D.; Sharon, A.; Maulikb, P. R.; Rama, V. J. Tetrahedron Lett. 2004, 45, 6273.   

[43] Ballini, R. Synthesis 1993, 687.

[44] Zhu, S.-L.; Yu, S.-Y.; Ma, D.-W. Angew. Chem., Int. Ed. 2008, 47, 545.

[45] Mitchell, C. E. T.; Brenner, S. E.; Ley, S. V. Chem. Commun. 2005, 41, 5346.

[46] Mei, K.; Jin, M.; Zhang, S.; Li, P.; Liu, W.; Chen, X.; Xue, F.; Duan, W.; Wang, W. Org. Lett. 2009, 11, 2864.

[47] Yang, Y.-Q.; Chen, X.-K.; Xiao, H.; Liu, W.; Zhao, G. Chem. Commun. 2010, 46, 4130.

[48] Chandrasekhar, S.; Kumar, T. P.; Haribabu, K.; Reddy, C. R. Tetrahedron: Asymmetry 2011, 22, 697.

[49] Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.

[50] O'Kenndy, R.; Thornes, R. D. Coumarins: Biology, Applications, and Mode of Action, 1st ed., Wiley, New York, 1997.   

[51] Lu, D.-F.; Li, Y.-J.; Gong, Y.-F. J. Org. Chem. 2010, 75, 6900.

[52] Smart, B. E. J. Fluorine Chem. 2001, 109, 3.

[53] Thayer, A. M. Chem. Eng. News 2006, 84, 27.

[54] Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 6119.

[55] Prakash, G. K. S.; Beier, P. Angew. Chem., Int. Ed. 2006, 45, 2172.

[56] Li, H.; Ji, Y.-F.; Li, J.; Zhang, S.-L.; Yu, C.-G.; Wang, W. Sci. China Chem. 2010, 53, 135.

[57] Müller, C. A.; Pfaltz, A. Angew. Chem., Int. Ed. 2008, 47, 3363.

[58] Teichert, A.; Pfaltz, A. Angew. Chem., Int. Ed. 2008, 47, 3360.

[59] Müller, C. A.; Markert, C.; Teichert, A.; Pfaltz, A. Chem. Commun. 2009, 45, 1607.

[60] Fleischer, I.; Pfaltz, A. Chem. Eur. J. 2010, 16, 95.   

[61] Zheng, Z.-L.; Perkins, B. L.; Ni, B. K. J. Am. Chem. Soc. 2010, 132, 50.

[62] Husmann, R.; Jörres, M.; Raabe, G.; Bolm, C. Chem. Eur. J. 2010, 16, 12549.   

[63] Tzeng, Z.-H.; Chen, H.-Y.; Huang, C.-T.; Chen, K. Tetrahedron Lett. 2008, 49, 4134.   

[64] Tzeng, Z.-H.; Chen, H.-Y.; Reddy, R. G.; Huang, C.-T.; Chen, K. Tetrahedron 2009, 65, 2879.   

[65] Chang, C.; Li, S.-H.; Reddy, R. J.; Chen, K. Adv. Synth. Catal. 2009, 351, 1273.

[66] Diéguez, M.; Pàmies, O.; Claver, C. Chem. Rev. 2004, 104, 3189.

[67] Mata, Y.; Diéguez, M.; Pàmies, O.; Woodward, S. J. Org. Chem. 2006, 71, 8159.

[68] Wang, L.; Liu, J.; Miao, T.; Zhou, W.; Li, P.-H.; Ren, K.; Zhang, X.-L. Adv. Synth. Catal. 2010, 352, 2571.

[69] Lombardo, M.; Chiarucci, M.; Trombini, C. Green Chem. 2009, 11, 574.   

[70] Lombardo, M.; Easwar, S.; Pasi, F.; Trombini, C. Adv. Synth. Catal. 2009, 351, 276.

[71] Lombardo, M.; Chiarucci, M.; Quintavalla, A.; Trombini, C. Adv. Synth. Catal. 2009, 351, 2801.

[72] Zhao, J.-Q.; Gan, L.-H. Eur. J. Org. Chem. 2009, 2661.

[73] Sakthivel, K.; Notz, W.; Bui, T. Barbas, C. F. J. Am. Chem. Soc. 2001, 123, 5260.

[74] List, B.; Pojerliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.

[75] Enders, D.; Seki, A. Synlett 2002, 26.

[76] Agarwal, J.; Peddinti, R. K. Tetrahedron Lett. 2011, 52, 117.   

[77] Reddy, R. J.; Kuan, H. H.; Chou, T. Y.; Chen, K. Chem. Eur. J. 2009, 15, 9294.   

[78] Whiting, M.; Tripp, J. C.; Lin, Y. C.; Lindstrom, W.; Olson, A. J.; Elder, J. H.; Sharpless, K. B.; Fokin, V. V. J. Med. Chem. 2006, 49, 7697.

[79] Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B. J. Med. Chem. 2005, 48, 499.

[80] Bertelsen, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296.

[81] Lu, D.-F.; Gong, Y.-F.; Wang, W.-Z. Adv. Synth. Catal. 2010, 352, 644.

[82] Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1520.

[83] Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.

[84] Jiang, X.-X.; Zhang, B.-Z.; Zhang, Y.-F.; Lin, L.; Yan, W.-J.; Wang, R. Chirality 2010, 22, 625.   

[85] He, T.-X.; Gu, Q.; Wu, X.-Y. Tetrahedron 2010, 66, 3195.   

[86] Chen, J.-R.; Zou, Y.-Q.; Fu, L.; Ren, F.; Tan, F.; Xiao, W.-J. Tetrahedron 2010, 66, 5367.   

[87] Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170.

[88] Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369.

[89] Zhang, X.-J.; Liu, S.-P.; Li, X.-M.; Yan, M.; Chan, A. S. C. Chem. Commun. 2009, 45, 833.

[90] Thomassigny, C.; Prim, D.; Greck, C. Tetrahedron Lett. 2006, 47, 1117.   

[91] Mei, R.-Q.; Xu, X.-Y.; Li, Y.-C.; Fu, J.-Y.; Huang, Q.-C.; Wang, L.-X. Tetrahedron Lett. 2011, 52, 1566.   

[92] Bai, J.-F.; Xu, X.-Y.; Huang, Q.-C.; Peng, L.; Wang, L.-X. Tetrahedron Lett. 2010, 51, 2803.   

[93] Cao, X.-Y.; Zheng, J.-C.; Li, Y.-X.; Shu, Z.-C.; Sun, X.-L.; Wang, B.-Q.; Tang, Y. Tetrahedron 2010, 66, 9703.   

[94] Chuan, Y.-M.; Yin, L.-Y.; Zhang, Y.-M.; Peng, Y.-G. Eur. J. Org. Chem. 2011, 578.   

[95] Marini, F.; Sternativo, S.; Verme, F. D.; Testaferri, L.; Tiecco, M. Adv. Synth. Catal. 2009, 351, 103.

[96] Tieceo, M.; Testaferri, L.; Temperini, A.; Bagnoli, L.; Marini, F.; Santi, C. Chem. Eur. J. 2004, 10, 1752.   

[97] Tieceo, M.; Carlone, A.; Sternativo, S.; Marini, F.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 6882.

[98] Li, X.; Xi, Z.-G.; Luo, S.-Z.; Cheng, J.-P. Org. Biomol. Chem. 2010, 8, 77.

[99] Ge, H.-M.; Zhu, C.-H.; Shi, D.-H.; Zhang, D.-L.; Xie, D.-Q.; Yang, J.; Ng, S. W.; Tan, R.-X. Chem. Eur. J. 2008, 14, 376.   

[100] Pe'rez-Fons, L.; Garzo'n, M. T.; Micol, V. J. Agric. Food Chem. 2010, 58, 161.

[101] Pertino, M. W.; Theoduloz, C.; Rodri'guez, J. A.; Lazo, V. J. Nat. Prod. 2010, 73, 639.

[102] Li, X.; Xue, X.-S.; Liu, C.; Wang, B.; Tan, B.-X.; Jin, J.-L.; Zhang, Y.-Y.; Dong, N.; Cheng, J.-P. Org. Biomol. Chem. 2012, 10, 413.

[103] Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899.

[104] Aleaine, A.; Marqués-López, E.; Merino, P.; Tejero, T.; Herrera, R. P. Org. Biomol. Chem. 2011, 9, 2777.

[105] Bui, T.; Syed, S.; Barbas III, C. F. J. Am. Chem. Soc. 2009, 131, 8758.

[106] Zhao, S.-L.; Zheng, C.-W.; Wang, H.-F.; Zhao, G. Adv. Synth. Catal. 2009, 351, 2811.

[107] Masamune, S.; Kim, C. U.; Wilson, K. E.; Spessard, G. O.; Georghiou, P. E.; Bates, G. S. J. Am. Chem. Soc. 1975, 97, 3512.

[108] Shao, H.; Rueter, J. K.; Goodman, M. J. Org. Chem. 1998, 63, 5240.

[109] Huang, H.-C.; Zhu, K.-L.; Wu, W.-B.; Jin, Z.-C.; Ye, J.-X. Chem. Commun. 2012, 48, 461.

[110] Ho, T. L. Carbocycle Construction in Terpene Synthesis, Wiley-VCH, Weinheim, Germany, 1988.   

[111] Bui, T.; Barbas III, C. F. Tetrahedron Lett. 2000, 41, 6951.   

[112] Wu, B.; Liu, G.-G.; Li, M.-Q.; Zhang, Y.; Zhang, S.-Y.; Qiu, J.-R.; Xu, X.-P.; Ji, S.-J.; Wang, X.-W. Chem. Commun. 2011, 47, 3992.

[113] Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404.

[114] Lee, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 15438.

[115] Liu, Y.-Z.; Cheng, R.-L.; Xu, P.-F. J. Org. Chem. 2011, 76, 2884.

[116] Liu, L.; Wu, D.-Y.; Zheng, S.; Li, T.-F.; Li, X.-M.; Wang, S.-N.; Li, J.; Li, H.; Wang, W. Org. Lett. 2012, 14, 134.

[117] Crosignani, S.; Page, P.; Missotten, M.; Colovray, V.; Cleva, C.; Arrighi, J. F.; Atherall, J.; Macritchie, J.; Martin, T.; Humbert, Y.; Gaudet, M.; Pupowicz, D.; Miao, M.; Pittet, P. A.; Golzio, L.; Giachetti, C.; Rocha, C.; Bernardinelli, G.; Filinchuk, Y.; Scheer, A.; Schwarz, M. K.; Chollet, A. J. Med. Chem. 2008, 51, 2227.

[118] Xu, D.-Q.; Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhong, A.-G.; Xia, A.-B.; Xu, Z.-Y. Chem. Eur. J. 2010, 16, 4177.   

[119] Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.

[120] Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257.

[121] Yang, W.; Du, D.-M. Org. Lett. 2010, 12, 5450.

[122] Yang, W.; Jia, Y.; Du, D.-M. Org. Biomol. Chem. 2012, 10, 332.

[123] Rao, H. S.; Oh, S. H.; Lee, J. W.; Lee, J. Y.; Chin, J.; Song, C. E. Chem. Commun. 2008, 44, 1208.

[124] Tárkáng, G.; Király, P.; Varga, S.; Vakulya, B.; Soós, T. Chem. Eur. J. 2008, 14, 6078.   

[125] Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278.

[126] Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1.

[127] O'Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532.

[128] Cai, Q.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 8666.

[129] Widianti, T.; Hiraga, Y.; Kojima, S.; Abe, M. Tetrahedron: Asymmetry 2010, 21, 1861.  

文章导航

/