SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 9: 1587 - 1604

DOI: https://doi.org/10.6023/cjoc201203009

Reviews

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)

Fold

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.

Key words： asymmetric Michael addition; organocatalysis; enantioselectivity; application

Cite this article

Ying , Anguo , Wu Chenglin , Fu Yongqian , Ren Shibin . Progress in the Application of Organocatalysis to Asymmetric Michael Additions[J]. Chinese Journal of Organic Chemistry, 2012 , 32(9) : 1587 -1604 . DOI: 10.6023/cjoc201203009

References

[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.  

Options
Outlines

/

〈 〉