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Stereoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with grignard reagents. Synthesis of naftifine

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Abstract

A general procedure for the synthesis of trans- and cis-allylamines has been developed on the basis of iron-catalyzed cross-coupling of Grignard reagents with stereochemically pure 3-chloroprop-2-en-1-amines prepared by allylation of amines with commercially available 1,3-dichloropropene isomers.

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References

  1. Bonjoch, J. and Sole, D., Chem. Rev. 2000, vol. 100, p. 3455; Shibasaki, M. and Ohshima, T., Alkaloids: Chem. Biol., 2007, vol. 64, p. 103.

    Article  CAS  Google Scholar 

  2. Kozmin, S.A., Iwama, T., Huang, Y., and Rawal, V.H., J. Am. Chem. Soc., 2002, vol. 124, p. 4628.

    Article  CAS  Google Scholar 

  3. Brosius, A.D. and Overman, L.E., J. Org. Chem., 1997, vol. 62, p. 440.

    Article  CAS  Google Scholar 

  4. Otake, N., Takeuchi, S., Endo, T., and Yonehara, H., Tetrahedron Lett., 1965, vol. 6, p. 1405.

    Article  Google Scholar 

  5. Kobayashi, K., Miyazawa, S., Terahara, A., Mishima, H., and Kurihara, H., Tetrahedron Lett., 1976, vol. 17, p. 537.

    Article  Google Scholar 

  6. Kameda, Y. and Horii, S., J. Chem. Soc., Chem. Commun., 1972, p. 746.

    Google Scholar 

  7. Jumnah, R., Williams, J.M.J., and Williams, A.C., Tetrahedron Lett., 1993, vol. 34, p. 6619; Bower, J.F., Jumnah, R., Williams, A.C., and Williams, J.M.J., J. Chem. Soc., Perkin Trans. 1, 1997, p. 1411; Burgess, K., Liu, L.T., and Pal, B., J. Org. Chem., 1993, vol. 58, p. 4758; Spangenberg, T., Schoenfelder, A., Breit, B., and Mann, A., Org. Lett., 2007, vol. 9, p. 3881.

    Article  CAS  Google Scholar 

  8. Martin, D.B.C., Nguyen, L.Q., and Vanderwal, C.D., J. Org. Chem., 2012, vol. 77, p. 17; Bennasar, M.-L., Sole, D., Zulaica, E., and Alonso, S., Org. Lett., 2011, vol. 13, p. 2042; Ramharter, J., Weinstabl, H., and Mulzer, J., J. Am. Chem. Soc., 2010, vol. 132, p. 14 338.

    Article  CAS  Google Scholar 

  9. Chen, X., Fan, Y., Zheng, Y., and Shen, Y., Chem. Rev., 2003, vol. 103, p. 1955.

    Article  CAS  Google Scholar 

  10. Gupta, A.K. and Shear, N.H., J. Am. Acad. Dermatol., 1997, vol. 37, p. 979.

    Article  CAS  Google Scholar 

  11. Monk, J.P. and Brogden, R.N., Drugs, 1991, vol. 42, p. 659.

    Article  CAS  Google Scholar 

  12. Cheikh, R.B., Chaabouni, R., Laurent, A., Mison, P., and Nafti, A., Synthesis, 1983, p. 685; Johannsen, M. and Jørgensen, K.A., Chem. Rev., 1998, vol. 98, p. 1689; Overman, L.E. and Carpenter, N.E., Org. React., 2005, vol. 66, p. 1; Ramirez, T.A., Zhao, B., and Shi, Y., Chem. Soc. Rev., 2012, vol. 41, p. 931.

    Google Scholar 

  13. Petasis, N.A. and Akritopoulou, I., Tetrahedron Lett., 1993, vol. 34, p. 583; Candeias, N.R., Montalbano, F., Cal, P.M.S.D., and Gois, P.M.P., Chem. Rev., 2010, vol. 110, p. 6169.

    Article  CAS  Google Scholar 

  14. Buchwald, S.L., Watson, B.T., Wannamaker, M.W., and Dewan, J.C., J. Am. Chem. Soc., 1989, vol. 111, p. 4486.

    Article  CAS  Google Scholar 

  15. Kakuuchi, A., Taguchi, T., and Hanzawa, Y., Tetrahedron Lett., 2003, vol. 44, p. 923.

    Article  CAS  Google Scholar 

  16. Wipf, P., Kendall, C., and Stephenson, C.R.J., J. Am. Chem. Soc., 2003, vol. 125, p. 761.

    Article  CAS  Google Scholar 

  17. Frantz, M.-C., Pierce, J.G., Pierce, J.M., Kangying, L., Qingwei, W., Johnson, M., and Wipf, P., Org. Lett., 2011, vol. 13, p. 2318.

    Article  CAS  Google Scholar 

  18. Wu, J., Marcoux, J.-F., Davies, I.W., and Reider, P.J., Tetrahedron Lett., 2001, vol. 42, p. 159.

    Article  CAS  Google Scholar 

  19. Olofsson, K., Larhed, M., and Hallberg, A., J. Org. Chem., 2000, vol. 65, p. 7235.

    Article  CAS  Google Scholar 

  20. Cacchi, S., Fabrizi, G., Goggiamani, A., and Sferrazza, A., Org. Biomol. Chem., 2011, vol. 9, p. 1727; Prediger, P., Barbosa, L.F., Genisson, Y., and Correia, C.R.D., J. Org. Chem., 2011, vol. 76, p. 7737.

    Article  CAS  Google Scholar 

  21. Xie, Y., Hu, J., Wang, Y., Xia, C., and Huang, H., J. Am. Chem. Soc., 2012, vol. 134, p. 20 613.

    Article  CAS  Google Scholar 

  22. Takhautdinova, A.U., Mindiyarova, E.R., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Appl. Chem., 2011, vol. 84, p. 504; Takhautdinova, A.U., Mindiyarova, E.R., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Appl. Chem., 2011, vol. 84, p. 504; Takhautdinova, A.U., Ishbaeva, A.U., Sunagatullina, A.Sh., Shakhmaev, R.N., and Zorin, V.V., Bash. Khim. Zh., 2010, vol. 17, p. 39.

    Article  CAS  Google Scholar 

  23. Sunagatullina, A.Sh., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Gen. Chem., 2013, vol. 83, p. 148; Sunagatullina, A.Sh., Shakhmaev, R.N., and Zorin, V.V., Russ. J. Org. Chem., 2013, vol. 49, p. 730.

    Article  CAS  Google Scholar 

  24. Knappke, C.E.I. and von Wangelin, A.J., Chem. Soc. Rev., 2011, vol. 40, p. 4948.

    Article  CAS  Google Scholar 

  25. Tamura, M. and Kochi, J., J. Am. Chem. Soc., 1971, vol. 93, p. 1487.

    Article  CAS  Google Scholar 

  26. Cahiez, G. and Avedissian, H., Synthesis, 1998, p. 1199.

    Google Scholar 

  27. Furstner, A. and Leitner, A., Angew. Chem., Int. Ed., 2002, vol. 41, p. 609; Furstner, A. and Leitner, A., Angew. Chem., Int. Ed., 2003, vol. 42, p. 308; Seidel, G., Laurich, D., and Furstner, A., J. Org. Chem., 2004, vol. 69, p. 3950; Gogsig, T.M., Lindhardt, A.T., and Skrydstrup, T., Org. Lett., 2009, vol. 11, p. 4886; Perry, M.C., Gillett, A.N., and Law, T.C., Tetrahedron Lett., 2012, vol. 53, p. 4436; Risatti, C., Natalie, K.J., Jr., Shi, Z., and Conlon, D.A., Org. Proc. Res. Dev., 2013, vol. 17, p. 257.

    Article  Google Scholar 

  28. Furstner, A., Leitner, A., Mendez, M., and Krause, H., J. Am. Chem. Soc., 2002, vol. 124, p. 13 856.

    Article  Google Scholar 

  29. Martin, R. and Furstner, A., Angew. Chem., Int. Ed., 2004, vol. 43, p. 3955; Nakamura, M., Matsuo, K., Ito, S., and Nakamura, E., J. Am. Chem. Soc., 2004, vol. 126, p. 3686; Nagano, T. and Hayashi, T., Org. Lett., 2004, vol. 6, p. 1297; Bedford, R.B., Bruce, D.W., Frost, R.M., Goodby, J.W., and Hird, M., Chem. Commun., 2004, p. 2822; Bedford, R.B., Bruce, D.W., Frost, R.M., and Hird, M., Chem. Commun., 2005, p. 4161; Bica, K. and Gaertner, P., Org. Lett., 2006, vol. 8, p. 733; Bedford, R.B., Betham, M., Bruce, D.W., Danopoulos, A.A., Frost, R.M., and Hird, M., J. Org. Chem., 2006, vol. 71, p. 1104; Cahiez, G., Habiak, V., Duplais, C., and Moyeux, A., Angew. Chem., Int. Ed., 2007, vol. 46, p. 4364; Chowdhury, R.R., Crane, A.K., Fowler, C., Kwong, P., and Kozak, C.M., Chem. Commun., 2008, p. 94; Furstner, A., Martin, R., Krause, H., Seidel, G., Goddard, R., and Lehmann, C.W., J. Am. Chem. Soc., 2008, vol. 130, p. 8773; Noda, D., Sunada, Y., Hatakeyama, T., Nakamura, M., and Nagashima, H., J. Am. Chem. Soc., 2009, vol. 131, p. 6078; Steib, A.K., Thaler, T., Komeyama, K., Mayer, P., and Knochel, P., Angew. Chem., Int. Ed., 2011, vol. 50, p. 3303; Yamaguchi, Y., Ando, H., Nagaya, M., Hinago, H., Ito, T., and Asami, M., Chem. Lett., 2011, vol. 40, p. 983; Jin, M. and Nakamura, M., Chem. Lett., 2011, vol. 40, p. 1012; Hatakeyama, T., Fujiwara, Y.-i., Okada, Y., Itoh, T., Hashimoto, T., Kawamura, S., Ogata, K., Takaya, H., and Nakamura, M., Chem. Lett., 2011, vol. 40, p. 1030.

    Article  CAS  Google Scholar 

  30. Quintin, J., Franck, X., Hocquemiller, R., and Figadere, B., Tetrahedron Lett., 2002, vol. 43, p. 3547; Kuzmina, O.M., Steib, A.K., Flubacher, D., and Knochel, P., Org. Lett., 2012, vol. 14, p. 4818.

    Article  CAS  Google Scholar 

  31. Dohle, W., Kopp, F., Cahiez, G., and Knochel, P., Synlett, 2001, p. 1901.

    Google Scholar 

  32. Guerinot, A., Reymond, S., and Cossy, J., Angew. Chem., Int. Ed., 2007, vol. 46, p. 6521; Cahiez, G., Duplais, C., and Moyeux, A., Org. Lett., 2007, vol. 9, p. 3253; Gregg, C., Gunawan, C., Ng, A.W.Y., Wimala, S., Wickremasinghe, S., and Rizzacasa, M.A., Org. Lett., 2013, vol. 15, p. 516.

    Article  CAS  Google Scholar 

  33. Hatakeyama, T., Yoshimoto, Y., Gabriel, T., and Nakamura, M., Org. Lett., 2008, vol. 10, p. 5341.

    Article  CAS  Google Scholar 

  34. Holmes, A.B. and Sporikou, C.N., Org. Synth., 1987, vol. 65, p. 61; Schwartz, A., Madan, P., Whitesell, J.K., and Lawrence, R.M., Org. Synth., 1990, vol. 69, p. 1.

    Article  CAS  Google Scholar 

  35. Wakefield, B.J., Organomagnesium Methods in Organic Synthesis, London: Academic, 1995.

    Google Scholar 

  36. Love, B.E. and Jones, E.G., J. Org. Chem., 1999, vol. 64, p. 3755.

    Article  CAS  Google Scholar 

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Correspondence to R. N. Shakhmaev.

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Original Russian Text © R.N. Shakhmaev, A.Sh. Sunagatullina, V.V. Zorin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 3, pp. 334–342.

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Shakhmaev, R.N., Sunagatullina, A.S. & Zorin, V.V. Stereoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with grignard reagents. Synthesis of naftifine. Russ J Org Chem 50, 322–331 (2014). https://doi.org/10.1134/S1070428014030038

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  • DOI: https://doi.org/10.1134/S1070428014030038

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