Pure and Applied Chemistry

Pure Appl. Chem., 2010, Vol. 82, No. 9, pp. 1827-1833

http://dx.doi.org/10.1351/PAC-CON-09-12-12

Published online 2010-06-28

Copper-catalyzed enantioselective aziridination of styrenes

References

• 1a. V. H. Dahanukar, I. A. Zavialov. Curr. Opin. Drug Discovery Dev. 5, 918 (2002).
• 1b. F. M. D. Ismail, D. O. Levitsky, V. M. Dembitsky. Eur. J. Med. Chem. 44, 3373 (2009). (http://dx.doi.org/10.1016/j.ejmech.2009.05.013)
• 2a. W. McCoull, F. A. Davis. Synthesis 1347 (2000). (http://dx.doi.org/10.1055/s-2000-7097)
• 2b. X. E. Hu. Tetrahedron 60, 2701 (2004). (http://dx.doi.org/10.1016/j.tet.2004.01.042)
• 2c. A. M. Taylor, S. L. Schreiber. Tetrahedron Lett. 50, 3230 (2009). (http://dx.doi.org/10.1016/j.tetlet.2009.02.034)
• 2d. Y. C. Wu, J. P. Zhu. Org. Lett. 11, 5558 (2009). (http://dx.doi.org/10.1021/ol9024919)
• 3. P. Dauban, G. Malik. Angew. Chem., Int. Ed. 48, 9026 (2009). (http://dx.doi.org/10.1002/anie.200904941)
• 4a. E. N. Jacobsen. In Comprehensive Asymmetric Catalysis, Vol. 2, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), pp. 607–618, Springer, Berlin (1999).
• 4b. J. B. Sweeney. Chem. Soc. Rev. 31, 247 (2002). (http://dx.doi.org/10.1039/b006015l)
• 4c. A. K. Yudin (Ed.). Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim (2006).
• 5. D. Tanner. Angew Chem., Int. Ed. 33, 599 (1994).
• 6a. G. S. Singh, M. D’Hooghe, N. De Kimpe. Chem. Rev. 107, 2080 (2007). (http://dx.doi.org/10.1021/cr0680033)
• 6b. J. Sweeney. Eur. J. Org. Chem. 4911 (2009). (http://dx.doi.org/10.1002/ejoc.200900211)
• 6c. Y. Zhang, Z. J. Lu, W. D. Wulff. Synlett 2715 (2009).
• 6d. S. Minakata. Acc. Chem. Res. 42, 1172 (2009). (http://dx.doi.org/10.1021/ar900059r)
• 7a. P. Muller, C. Fruit. Chem. Rev. 103, 2905 (2003). (http://dx.doi.org/10.1021/cr020043t)
• 7b. J. A. Halfen. Curr. Org. Chem. 9, 657 (2005). (http://dx.doi.org/10.2174/1385272053765024)
• 8. See also: I. D. G. Watson, L. L. Yu, A. K. Yudin. Acc. Chem. Res. 39, 194 (2006). (http://dx.doi.org/10.1021/ar050038m)
• 9. P. Dauban, R. H. Dodd. Synlett 1571 (2003). (http://dx.doi.org/10.1055/s-2003-41010)
• 10a. D. Mansuy, J. P. Mahy, A. Dureault, G. Bedi, P. Battioni. J. Chem. Soc., Chem. Commun. 1161 (1984). (http://dx.doi.org/10.1039/c39840001161)
• 10b. J. P. Mahy, P. Battioni, D. Mansuy. J. Am. Chem. Soc. 108, 1079 (1986). (http://dx.doi.org/10.1021/ja00265a037)
• 10c. J. P. Mahy, G. Bedi, P. Battioni, D. Mansuy. J. Chem. Soc., Perkin Trans. 2 1517 (1988). (http://dx.doi.org/10.1039/p29880001517)
• 11a. S. M. Au, S. B. Zhang, W. H. Fung, W. Y. Yu, C. M. Che, K. K. Cheung. Chem. Commun. 2677 (1998). (http://dx.doi.org/10.1039/a808048h)
• 11b. S. M. Au, J. S. Huang, W. Y. Yu, W. H. Fung, C. M. Che. J. Am. Chem. Soc. 121, 9120 (1999). (http://dx.doi.org/10.1021/ja9913481)
• 11c. X. G. Zhou, X. Q. Yu, J. S. Huang, C. M. Che. Chem. Commun. 2377 (1999). (http://dx.doi.org/10.1039/a907653k)
• 11d. J. L. Liang, J. S. Huang, X. Q. Yu, N. Y. Zhu, C. M. Che. Chem.—Eur. J. 8, 1563 (2002). (http://dx.doi.org/10.1002/1521-3765(20020402)8:7<1563::AID-CHEM1563>3.0.CO;2-V)
• 12a. J. E. Jones, J. V. Ruppel, G. Y. Gao, T. M. Moore, X. P. Zhang. J. Org. Chem. 73, 7260 (2008). (http://dx.doi.org/10.1021/jo801151x)
• 12b. V. Subbarayan, J. V. Ruppel, S. Zhu, J. A. Perman, X. P. Zhang. Chem. Commun. 4266 (2009). (http://dx.doi.org/10.1039/b905727g)
• 13a. D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, D. M. Barnes. J. Am. Chem. Soc. 115, 5328 (1993). (http://dx.doi.org/10.1021/ja00065a068)
• 13b. E. N. Jacobsen, Z. Li, K. R. Conser. J. Am. Chem. Soc. 115, 5326 (1993).
• 14a. M. J. Sodergren, D. A. Alonso, P. G. Andersson. Tetrahedron: Asymmetry 8, 3563 (1997). (http://dx.doi.org/10.1016/S0957-4166(97)00496-5)
• 14b. C. J. Sanders, K. M. Gillespie, D. Bell, P. Scott. J. Am. Chem. Soc. 122, 7132 (2000). (http://dx.doi.org/10.1021/ja994353d)
• 14c. M. Gillespie, C. J. Sanders, P. O’Shaughnessy, I. Westmoreland, C. P. Thickitt, P. Scott. J. Org. Chem. 67, 3450 (2002). (http://dx.doi.org/10.1021/jo025515i)
• 14d. P. H. Di Chenna, F. Robert-Peillard, P. Dauban, R. H. Dodd. Org. Lett. 6, 4503 (2004). (http://dx.doi.org/10.1021/ol048167a)
• 14e. J. X. Xu, L. G. Ma, P. Jiao. Chem. Commun. 1616 (2004). (http://dx.doi.org/10.1039/b404134h)
• 14f. L. G. Ma, P. Jiao, Q. H. Zhang, J. X. Xu. Tetrahedron: Asymmetry 16, 3718 (2005). (http://dx.doi.org/10.1016/j.tetasy.2005.09.025)
• 14g. L. Ma, D. M. Du, J. X. Xu. Chirality 18, 575 (2006). (http://dx.doi.org/10.1002/chir.20282)
• 14h. X. S. Wang, K. L. Ding. Chem.—Eur. J. 12, 4568 (2006). (http://dx.doi.org/10.1002/chem.200501109)
• 14i. A. Esteoule, F. Duran, P. Retailleau, R. H. Dodd, P. Dauban. Synthesis 1251 (2007).
• 15. H. Kawabata, K. Omura, T. Uchida, T. Katsuki. Chem. Asian J. 2, 248 (2007). (http://dx.doi.org/10.1002/asia.200600363)
• 16a. P. Muller, C. Baud, Y. Jacquier. Can. J. Chem. 76, 738 (1998). (http://dx.doi.org/10.1139/cjc-76-6-738)
• 16b. J. L. Liang, S. X. Yuan, P. W. H. Chan, C. M. Che. Tetrahedron Lett. 44, 5917 (2003). (http://dx.doi.org/10.1016/S0040-4039(03)01409-6)
• 16c. C. Fruit, F. Robert-Peillard, G. Bernardinelli, P. Muller, R. H. Dodd, P. Dauban. Tetrahedron: Asymmetry 16, 3484 (2005). (http://dx.doi.org/10.1016/j.tetasy.2005.07.005)
• 16d. M. Yamawaki, M. Tanaka, T. Abe, M. Anada, S. Hashimoto. Heterocycles 72, 709 (2007).
• 17. P. Dauban, R. H. Dodd. J. Org. Chem. 64, 5304 (1999). (http://dx.doi.org/10.1021/jo990356x)
• 18a. H. Lebel, K. Huard, S. Lectard. J. Am. Chem. Soc. 127, 14198 (2005). (http://dx.doi.org/10.1021/ja0552850)
• 18b. H. Lebel, O. Leogane, K. Huard, S. Lectard. Pure Appl. Chem. 78, 363 (2006). (http://dx.doi.org/10.1351/pac200678020363)
• 19. K. Huard, H. Lebel. Chem.—Eur. J. 14, 6222 (2008). (http://dx.doi.org/10.1002/chem.200702027)
• 20. K. Huard, H. Lebel. Org. Synth. 86, 59 (2009).
• 21. H. Lebel, K. Huard. Org. Lett. 9, 639 (2007). (http://dx.doi.org/10.1021/ol062953t)
• 22a. M. K. Madhra, M. Sharma, C. H. Khanduri. Org. Process Res. Dev. 11, 922 (2007). (http://dx.doi.org/10.1021/op700138p)
• 22b. J. M. Reddy, G. Prasad, V. Raju, M. Ravikumar, V. Himabindu, G. M. Reddy. Org. Process Res. Dev. 11, 268 (2007). (http://dx.doi.org/10.1021/op060246+)
• 23. H. Lebel, S. Lectard, M. Parmentier. Org. Lett. 9, 4797 (2007). (http://dx.doi.org/10.1021/ol702152e)
• 24. Copper(I) salts were selected over copper(II) salts, as mechanistic studies indicate that the actual catalytic cycle for aziridination reactions involves Cu(I)-Cu(III) redox mechanism, see.
• 24a. Z. Li, R. W. Quan, E. N. Jacobsen. J. Am. Chem. Soc. 117, 5889 (1995). (http://dx.doi.org/10.1021/ja00126a044)
• 24b. P. Brandt, M. J. Sodergren, P. G. Andersson, P. O. Norrby. J. Am. Chem. Soc. 122, 8013 (2000). (http://dx.doi.org/10.1021/ja993246g)
• 24c. K. M. Gillespie, E. J. Crust, R. J. Deeth, P. Scott. Chem. Commun. 785 (2001). (http://dx.doi.org/10.1039/b101415n)
• 24d. P. Comba, C. L. Lang, C. L. de Laorden, A. Muruganantham, G. Rajaraman, H. Wadepold, M. Zajaczkowski. Chem.—Eur. J. 14, 5313 (2008). (http://dx.doi.org/10.1002/chem.200701910)