Progress in Copper-Catalyzed Asymmetric Allylic Alkylation Reaction

doi:10.6023/cjoc1110071

Abstract

Copper-catalyzed asymmetric allylic alkylation reaction is one of the most important methods for preparing chiral compounds. The recent progress of copper-catalyzed asymmetric allylic alkylation reaction is reviewed. Great attention is paid to the influences caused by the structure of allylic derivatives and chiral ligands and the type of nucleophiles on this kind of allylic alkylation reaction.

Key words: copper-catalysis, chiral compound, allylic derivative, asymmetric allylic alkylation reaction

Cite this article

Cui Penglei, Liu Haiyan, Zhang Dongnuan, Wang Chun. Progress in Copper-Catalyzed Asymmetric Allylic Alkylation Reaction[J]. Chin. J. Org. Chem., 2012, 32(08): 1401-1409.

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References

[1] Takeuchi, R. Polyhedron 1999, 19, 557.

[2] Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.

[3] Gunasekara, N. G.; Noble, S.; Benfield, P. Drugs 1998, 55, 85.

[4] Miyabe, H.; Takemoto, Y. Synlett 2005, 1641.

[5] Trost, B. M. J. Org. Chem. 2004, 69, 5813.

[6] Wu, Y.-J.; Yang, D.-Q.; Long, Y.-H. Chin. J. Org. Chem. 2009, 29, 1522 (in Chinese). (吴钰娟, 杨定乔, 龙玉华, 有机化学, 2009, 29, 1522.)

[7] Wang, Y.-F.; Zeng, J.-H.; Cui, X.-R. Chin. J. Org. Chem. 2010, 30, 181 (in Chinese). (王晔峰, 曾京辉, 崔晓瑞, 有机化学, 2010, 30, 181.)

[8] Xu, H.-J.; Man, Q.-S.; Lin, Y.-C.; Li, Y.-Y.; Feng, Y.-S. Chin. J. Org. Chem. 2010, 30, 9 (in Chinese). (许华建, 蔄秋石, 林义成, 李源源, 冯乙巳, 有机化学, 2010, 30, 9.)

[9] Qin, Y.-C.; Peng, Q. Chin. J. Org. Chem. 2011, 31, 1169 (in Chinese). (秦元成, 彭强, 有机化学, 2011, 31, 1169.)

[10] Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435.

[11] Kar, A.; Argade, N. P. Synthesis 2005, 2995.

[12] Goering, H. L.; Singleton Jr, V. D. J. Am. Chem. Soc. 1976, 98, 7854.

[13] Goering, H. L.; Kantar, S. S. J. Org. Chem. 1984, 49, 422.

[14] Goering, H. L.; Singleton Jr, V. D. J. Am. Chem. Soc. 1983, 48, 1531.

[15] Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063.

[16] Bertz, S. H.; Dabbagh, G.; Mujsce, A. M. J. Am. Chem. Soc. 1991, 113, 631.

[17] Berlan, J.; Battioni, J. P.; Koosha, K. J. Organomet. Chem. 1978, 152, 359.

[18] Lipshutz in, B. H. Organomet. Synth. 1994, 4, 283.

[19] Persson, E. S. M.; van Klaveren, M.; Grove, D. M.; B?ckvall, J. E.; van Koten, G. Chem. Eur. J. 1995, 1, 351.

[20] Karlstr?m, A. S. E.; B?ckvall, J. E. Chem. Eur. J. 2001, 7, 1981.

[21] van klaveren, M.; Persson, E. S. M.; del Villar, A.; Grove, D. M.; B?ckvall, J.-E.; van Koten, G. Tetrahedron Lett. 1995, 36, 3059.

[22] Meuzwlaar, G. J.; Karlstrom, A. S. E.; Van Klaveren, M.; Persson, E. S. M.; Del Villar, A.; van Koten, G.; B?ckvall, J. E. Tetrahedron 2000, 56, 2895.

[23] Karlstr?m, A. S. E.; Huerta, F. F.; Meuzelaar, G. J. B?ckvall, J. E. Synlett 2001, 923.

[24] Alexakis, A.; Malan, C.; Lea, L.; Benhaim, C.; Fournioux, X. Synlett 2001, 927.

[25] Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147.

[26] Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426.

[27] Tissot-Croset, K.; Polet, D.; Gille, S.; Hawner, C.; Alexakis, A. Synthesis 2004, 2586.

[28] Tissot-Croset, K.; Alexakis, A. Tetrahedron Lett. 2004, 45, 7375.

[29] Falciola, C. A.; Tissot-Croset, K.; Alexakis, A. Angew. Chem., Int. Ed. 2006, 45, 5995.

[30] Tominaga, S.; Oi, Y.; Kato, T.; An, D. K.; Okamato, S. Tetrahedron Lett. 2004, 45, 5585.

[31] Okamato, S.; Tominaga, S.; Saino, N.; Kase, K.; Shimoda, K. J. Organomet. Chem. 2005, 690, 6001.

[32] Lopez, F.; Van Zijl, A. W.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2006, 409.

[33] Van Zijl, A. W.; Lopez, F.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2007, 72, 2558.

[34] Geurts, K. Fletcher, S. P.; Feringa, B. L. J. Am. Chem. Soc. 2006. 128, 15572.

[35] Teichert, J. F.; Zhang, S. Y.; van Zijl, A. W.; Slaa, J. W.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2010, 12, 4658.

[36] Selim, K. B.; Matsumoto, Y.; Yamada, K.; Tomioka, K. Angew. Chem., Int. Ed. 2009, 48, 8733.

[37] Mastral, M. F.; Horst, B.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2011, 47, 5843.

[38] Dubner, F.; Knochel, P. Angew. Chem., Int. Ed. 1998, 38, 379.

[39] Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233.

[40] Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169.

[41] van Zijl, A. W.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2004, 346, 413.

[42] Borner, C.; Goldsmith, P. J.; Woodward, S.; Gimeno, J.; Gladiali, S.; Ramazzotti, D. Chem. Commun. 2000, 2433.

[43] Bennet, S. M. W.; Brown, S. M.; Cunningham, A.; Dennis, M. R.; Muxworthy, J. P.; Oakley, M. A.; Woodward, S. Tetrahedron 2000, 56, 2847.

[44] Goldsmith, P. J.; Teat, S. J.; Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 2235.

[45] Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456.

[46] Murphy, K. E.; Hoveyda, A. H.; J. Am. Chem. Soc. 2003. 125, 4690.

[47] Hoveyda, A. H.; Hird, A. W.; Kacprzynski, M. A. Chem. Commun. 2004, 1799.

[48] Kacprzynski, M. A. Hoveyda, A. H. J. Am. Chem. Soc. 2004. 126, 10676.

[49] Piarulli, U.; Daubos, P.; Claverie, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234.

[50] Piarulli, U.; Claverie, C.; Daubos, P.; Gennari, C.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 4493.

[51] Larsen, A. O.; Leu, W.; Oberhuber, C. N.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 11130.

[52] Kacprzynski, M. A.; May, T. L.; Kazane, S. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4554.

[53] Gillingham, D. G.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 3860.

[54] Lee, Y.; Akiyama, K.; Gillingham, D. G.; Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008. 130, 446.

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