Journal of the Iranian Chemical Society

, Volume 5, Issue 3, pp 384–393 | Cite as

Sulfamic acid catalyzed ring opening of epoxides with amines under solvent-free conditions



Sulfamic acid (SA) catalyses the nucleophilic opening of epoxide rings by amines leading to the efficient synthesis of ß-amino alcohols. The reaction works well with aromatic and aliphatic amines in short reaction times and in the absence of solvent. Exclusive trans stereoselectivity is observed for the ring opening of cyclohexene oxide. This method exhibits excellent regioselectivity for preferential nucleophilic attack at the less hindered position during the reaction with unsymmetrical epoxides.


Sulfamic acid Epoxide Amines ß-Amino alcohols 


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References and Notes

  1. [1]a)
    C. Bonini, G. Righi, Synthesis (1994) 225Google Scholar
  2. [1]b)
    H. Sharghi, A. Hassani-Nejad, M.A. Nasseri, New J. Chem. 28 (2004) 946 and references therein.Google Scholar
  3. [1]c)
    H. Sharghi, H. Naeimi, Bull. Chem. Soc. Jpn. 72 (1999) 1525Google Scholar
  4. [1]d)
    B. Tamami, N. Iranpoor, R. Rezaei, Synth. Commun. 35 (2004) 2789Google Scholar
  5. [1]e)
    N. Iranpoor, H. Firouzabadi, A. Safavi, M. Shekarriz, Synth. Commun. 32 (2002) 2287Google Scholar
  6. [1]f)
    N. Iranpoor, H. Firouzabadi, M. Shekarriz, Org. Biomol. Chem. 1 (2003) 724Google Scholar
  7. [1]g)
    H. Firouzabadi, N. Iranpoor, A.A. Jafari, S. Makarem, J. Mol. Cat. A: Chemical 250 (2006) 237.Google Scholar
  8. [2]
    In 1995, thirteen of the top two hundred drugs ranked by prescription volume were ethanolamine-based compounds (source: Pharmacy Times, April 1996).Google Scholar
  9. [3]a)
    G. Sekar, V.K. Singh, J. Org. Chem. 64 (1999) 287Google Scholar
  10. [3]b)
    T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 45 (2004) 49Google Scholar
  11. [3]c)
    I. Cepanec, M. Litvic, H. Mikuldas, A. Bartolincic, V. Vinkovie, Tetrahedron Lett. 44 (2003) 2435Google Scholar
  12. [3]d)
    F. Fringuelli, F. Pizzo, S. Tortoioli, L. Vaccaro, J. Org. Chem. 69 (2004) 7745.Google Scholar
  13. [4]a)
    L.R. Reddy, M.A. Reddy, N. Bhanumathi, K.R. Rao, New J. Chem. 25 (2001) 221Google Scholar
  14. [4]b)
    L. Duran Pachon, P. Gamez, J.J.M. Van Brussel, J. Reedijk, Tetrahedron Lett. 44 (2003) 6025Google Scholar
  15. [4]c)
    A. Chakraborti, A. Kondaskar, Tetrahedron Lett. 44 (2003) 8315Google Scholar
  16. [4]d)
    J.R. Rodriguez, A. Navarro, Tetrahedron Lett. 45 (2004) 7495Google Scholar
  17. [4]e)
    S. Chandrasekhar, T. Ramachandar, J.S. Prakash, Synthesis (2000) 1817Google Scholar
  18. [4]f)
    G. Sundarajan, K. Vijayakrishna, B. Varghese, Tetrahedron Lett. 45 (2004) 8253Google Scholar
  19. [4]g)
    M.M. Alam, R. Varala, R. Enugala, S.R. Adapa, Lett. Org. Chem. 3 (2006) 187Google Scholar
  20. [4]h)
    M.R. Saidi, J. Chem. Res. (1999) 128.Google Scholar
  21. [5]
    V.R. Yarapathy, S. Mekala, B.V. Rao, S. Tammishetti, Catalysis Commun. 7 (2006) 466.Google Scholar
  22. [6]
    A.K. Chakraborti, A. Kondskar, S. Rudrawar, Tetrahedron 60 (2004) 9085.Google Scholar
  23. [7]a)
    P.-Q. Zhao, L.-W. Xu, C.-G. Xia, Synlett 5 (2004) 846Google Scholar
  24. [7]b)
    M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, Eur. J. Org. Chem. (2001) 4149.Google Scholar
  25. [8]a)
    U. Das, B. Crousse, V. Kesavan, D. Bonnet-Delpon, J.-P. Begue, J. Org. Chem. 65 (2000) 6749Google Scholar
  26. [8]b)
    J.S. Yadav, B.V.S. Reddy, A.K. Basak, A. Venkat Narsaiah, Tetrahedron Lett. 44 (2003) 1047Google Scholar
  27. [8]c)
    F.-S. Liang, A. Brik, Y.-C. Lin, J.H. Elder, C.-H. Wong, Bioorg. Med. Chem. 14 (2006) 1058. H. Eshghi, M. Rahimizadeh, A. Shoryabi, J. Iran. Chem. Soc. 2 (2005) 155.Google Scholar
  28. [9]a)
    T.S. Jin, G. Sun, Y.W. Li, T.S. Li, Green Chem. 4 (2002) 255Google Scholar
  29. [9]b)
    T.S. Jin, G. Sun, Y.W. Li, T.S. Li, J. Chem. Res., Synop. (2003) 30Google Scholar
  30. [9]c)
    T.S. Jin, Y.R. Ma, Z.H. Zhang, T.S. Li, Synth. Commun. 28 (1998) 3173Google Scholar
  31. [9]d)
    J. Chen, J.Y. Wu, Special. Petrochem. 3 (2001) 35Google Scholar
  32. [9]e)
    M.J. Rhoad, P.J. Hory, J. Am. Chem. Soc. 72 (1950) 2216Google Scholar
  33. [9]f)
    B. Wang, Y.L. Gu, G.Y. Luo, T. Yang, L.M. Yang, J.S. Suo, Tetrahedron Lett. 45 (2004) 3369Google Scholar
  34. [9]g)
    R. Nagarajan, C.J. Magesh, P.T. Perumal, Synthesis (2004) 69Google Scholar
  35. [9]h)
    P.R. Singh, D.U. Singh, S.D. Samant, Synlett (2004) 1909Google Scholar
  36. [9]i)
    J.T. Li, J.F. Han, J.H. Yang, T.S. Li, Ultrason. Sonochem. 10 (2003) 119Google Scholar
  37. [9]j)
    T.S. Jin, S.L. Zhang, S.Y. Zhang, J.J. Guo, T.S. Li, J. Chem. Res., Synop. (2002) 37Google Scholar
  38. [9]k)
    Z. Li, X. Ren, P. Wei, H. Wan, Y.P. Shi Ouyang, Green Chem. 8 (2006) 433.Google Scholar
  39. [10]a)
    M. Hosseini Sarvari, H. Sharghi, J. Org. Chem. 69 (2004) 6953Google Scholar
  40. [10]b)
    H. Sharghi, M. Hosseini Sarvari, Synthesis 8 (2002) 1057Google Scholar
  41. [10]c)
    M. Hosseini Sarvari, Synthesis 5 (2005) 787Google Scholar
  42. [10]d)
    M. Hosseini Sarvari, H. Sharghi, Tetrahedron 61 (2005) 10903Google Scholar
  43. [10]e)
    Y.J. Kim, R.S. Varma, Tetrahedron Lett. 45 (2004) 7205Google Scholar
  44. [10]f)
    M. Hosseini Sarvari, H. Sharghi, J. Org. Chem. 71 (2006) 6652.Google Scholar
  45. [11]
    G.S. Harbison, Y.-S. Kye, G.H. Penner, M. Grandin, M. Monette, J. Phys. Chem. B 106 (2002) 10285.Google Scholar

Copyright information

© Iranian Chemical Society 2008

Authors and Affiliations

  1. 1.Department of Chemistry, College of ScienceShiraz UniversityShirazIran

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