Skip to main content
SpringerLink
Log in

Synthesis methods of (1-aminocyclopropyl)phosphonic acids

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Known methods of preparation of (1-aminocyclopropyl)phosphonic acids and their derivatives are analyzed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Yang, S.F. and Hoffman, N.E., Ann. Rev. Plant, Physiol., 1984, vol. 35, p. 155.

    Article  CAS  Google Scholar 

  2. Pirrung, M.C., Acc. Chem. Res., 1999, vol. 32, p. 711.

    Article  CAS  Google Scholar 

  3. Pirrung, M.C., J. Am. Chem. Soc., 1983, vol. 105, p. 7207.

    Article  CAS  Google Scholar 

  4. Cativiela, C. and Ordusez, M., Tetrahedron: Asymmetry., 2009, vol. 20, p. 1.

    Article  CAS  Google Scholar 

  5. Brackmann, F., and de Mejere, A., Chem. Rev., 2007, vol. 107, p. 4493.

    Article  CAS  Google Scholar 

  6. Orsini, F., Sello, G., and Sisti, M., Cur. Med. Chem., 2010, vol. 17, p. 264.

    Article  CAS  Google Scholar 

  7. Aminophosphinic and Aminophosphonic Acids: Chemistry and Biological Activity, Kukhar, V.P. and Hudson, H.R., Eds., Chichester: J. Wiley & Sons Inc., 1999.

    Google Scholar 

  8. Ordusez, M., Rojas-Cabrera, H., and Cativiela, C., Tetrahedron, 2009, vol. 65, p. 17.

    Article  Google Scholar 

  9. Halab, L., Gosselin, F., and Lubell, W.D., Biopolymers, (Pept. Sci.)., 2000, vol. 55, p. 101.

    Article  CAS  Google Scholar 

  10. Pellicciari, R., Marinozzi, M., Camaioni, E., del Carmen Nshchnez, M., Costantino, G., Gasparini, F., Giorgi, G., Macchiarulo, A., and Subramanian, N., J. Org. Chem., 2002, vol. 67, p. 5497.

    Article  CAS  Google Scholar 

  11. Hruby, V.J., Li, G., Haskell-Luevano, C., and Shenderovich, M., Biopolymers (Pept. Sci.), 1997, vol. 43, p. 219.

    Article  CAS  Google Scholar 

  12. Vijayalakshmi, S., Rao, R.B., Karle, I.L., and Balaram, P., Biopolymers, 2000, vol. 53, p. 84

    Article  CAS  Google Scholar 

  13. Erion, M.D. and Walsh, C.T., Biochem., 1987, vol. 26, p. 3417.

    Article  CAS  Google Scholar 

  14. Karthikeyan, S., Zhao, Z., Kao, C., Zhou, Q., Tao, Z., Zhang, H., and Liu, H., Angew. Chem., Int. Ed., 2004, vol. 43, p. 3425.

    Article  CAS  Google Scholar 

  15. Karthikeyan, S., Zhou, Q., Zhao, Z., Kao, C., Tao, Z., Robinson, H., Liu, H., and Zhang, H., Biochem., 2004, vol. 43, p. 13328.

    Article  CAS  Google Scholar 

  16. Liverton, N.J., Summa, V., and Vacca, J.P., WO Inventor’s Certificate 2008051475; Chem. Abstr., 2008, vol. 148, 496354.

    Google Scholar 

  17. Liverton, N.J., Summa, V., Vacca, J.P., Di, Francesco, E.M., and Pompei, M., WO Inventor’s Certificate 2008051477; Chem. Abstr., 2008, 148, 496351; Pompei, M., Di, Francesco, E.M., Koch, U., Liverton, N.J., and Summa, V., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2574.

    Google Scholar 

  18. Casarez, A., Chaudhary, K., Cho, A., Clarke, M., Doerffler, E., Fardis, M., Kim, C.U., Pyun, H., Sheng, X.C., and Wang, J., WO Inventor’s Certificate, 2008005565; Chem. Abstr., 2008, vol. 148, 144883.

    Google Scholar 

  19. Casarez, A., Chaudhary, K., Kim, C.U., McMurtrie, D., Sheng, X.C., WO Inventor’s Certificate 2007011658; Chem. Abstr., 2007, vol. 146, 184741.

    Google Scholar 

  20. Chaudnary, K., Fleury, M., Kim, C.U., McMurtrie, D., Sheng, X.C., WO Inventor’s Certificate 2006020276; Chem. Abstr., 2006, vol. 144, 254385; Sheng, X.C., Pyun, H., Chaudhary, K., Wang, J., Doerffler, E., Fleury, M., McMurtrie, D., Chen, X., Delaney, W.E., and Kim, C.U., Bioorg. Med. Chem. Lett., 2009, 19, p. 3453; Pyun, H., Chaudhary, K., Somoza, J.R., Sheng, X.C., and Kim, C.U., Tetrahedron Lett., 2009, vol. 50, p. 3833.

    Google Scholar 

  21. Diel, P.J. and Maier, L., Phosphorus and Sulfur, 1984, vol. 20, p. 313.

    Article  CAS  Google Scholar 

  22. Groth, U., Lehmann, L., Richter, L., and Schtsllkopf, U., Lieb. Ann., 1993, p. 427.

  23. Rachos, J., Schtsllkopf, U., and Wintel, T., Lieb. Ann., 1981, p. 709.

  24. Davidsen, S.K., Phllips, G.W., and Martin, S.F., Org. Synth., 1993, vol. 8, p. 451.

    Google Scholar 

  25. Fadel, A. and Tesson, N., Eur. J. Org. Chem., 2000, p. 2153.

  26. Fadel, A., J. Org. Chem., 1999, vol. 64, p. 4953.

    Article  CAS  Google Scholar 

  27. Sala’n, J. and Marguerite, J. Org. Synth., 1990, vol. 7, p. 131.

    Google Scholar 

  28. Fadel, A. and Khesrani, A., Tetrahedron: Asymmetry, 1998, vol. 9, p. 305.

    Article  CAS  Google Scholar 

  29. Tesson, N., Dorigneux, B., and Fadel, A., Tetrahedron: Asymmetry, 2002, vol. 13, p. 2267.

    Article  CAS  Google Scholar 

  30. Fadel, A. and Tesson, N., Tetrahedron: Asymmetry, 2000, vol. 11, p. 2023.

    Article  CAS  Google Scholar 

  31. Hercouet, A., Le, Corre, M., and Carboni, B., Tetrahedron Lett., 2000, vol. 41, p. 197.

    Article  CAS  Google Scholar 

  32. Moore, J.D., Sprott, K.T., and Hanson, P.R., J. Org. Chem., 2002, vol. 67, p. 8123.

    Article  CAS  Google Scholar 

  33. Shioiri, T., Ninomiya, K., and Yamada, S., J. Am. Chem. Soc., 1972, vol. 94, p. 6203.

    Article  CAS  Google Scholar 

  34. Yamazaki, S., Takada, T., Imanishi, T., Moriguchi, Y., and Yamabe, S., J. Org. Chem., 1998, 63, 5919; Wąsek, K., Kkdzia, J., and Krawczyk, H., Tetrahedron: Asymmetry, 2010, vol. 21, p. 2081.

    Article  CAS  Google Scholar 

  35. Jászay, Z.M., Keserü, G.M., Clementis, G., Petneházy, I., Kováts, K., and Tkhke, L., Heteroatom, Chem., 2001, vol. 12, p. 90.

    Article  Google Scholar 

  36. Chemagin, A.V., Cand Sci. (Chem.) Dissertation, Moscow, 2010.

  37. Griffiths, G.F., Kenner, G.W., McCombie, S.W., Smith, K.M., and Sutton, M.J., Tetrahedron, 1976, 32, p. 275.

    Article  CAS  Google Scholar 

  38. Gao, Y. and Sharpless, K.B., J. Am. Chem. Soc., 1988, vol. 110, p. 7538.

    Article  CAS  Google Scholar 

  39. Shikari, C., Saito, H., Takahashi, K., Urakawa, C., and Hirata, T., Synthesis, 1988, p. 399.

  40. Reetz, M.T., Peter, R., and von Itzstein, M., Chem. Ber., 1987, vol. 120, p. 121.

    Article  CAS  Google Scholar 

  41. Takagi, R., Nakamura, M., Hashizume, M., Kojima, S., and Ohkata, K., Tetrahedron, Lett., 2001, vol. 42, p. 5891.

    Article  CAS  Google Scholar 

  42. Tkhke, L., Jászay, Z.M., Petneházy, I., Clementis, G., Vereczkey, G.D., Kövesdi, I., Rockenbauer, A., and Kovöts, K., Tetrahedron, 1995, vol. 51, p. 9167.

    Article  Google Scholar 

  43. Hanson, P.R., Sprott, K.T., and Wrobleski, A.D., Tetrahedron Lett., 1999, vol. 40, 1455; Moore, J.D., Sprott, K.T., Wrobleski, A.D, and Hanson, P.R., Org. Lett., 2002, vol. 4, 2357; Moore, J.D. and Hanson, P.R., Tetrahedron: Asymmetry, 2003, vol. 14, p. 873.

    Article  CAS  Google Scholar 

  44. Chemagin, A.V., Yashin, N.V., Grishin, Y.K, Kuznetsova, T.S., and Zefirov, N.S., Synthesis, 2010, p. 3379.

  45. Wurz, R.P. and Charette, A.B., J. Org. Chem., 2004, vol. 69, p. 1262.

    Article  CAS  Google Scholar 

  46. Chemagin, A.V., Yashin, N.V., Grishin, Y.K, Kuznetsova, T.S., and Zefirov, N.S., Synthesis, 2010, p. 259.

  47. Petrov, K.A., Chauzov, V.A., Bogdanov, N.N., and Pastukhova, I.V., Zh. Org. Khim., 1974, vol. 44, p. 1649.

    CAS  Google Scholar 

  48. Neimysheva, A.A. Muratov, S.S., Smirnov, E.V., and Solntseva, L.M., Zh. Obshch. Khim., 1976, vol. 46, p. 940.

    CAS  Google Scholar 

  49. Petrov, K.A., Chauzov, V.A., Bogdanov, N.N., Pastukhova, I.V., Zh. Obshch. Khim., 1976, vol. 46, p. 1242.

    CAS  Google Scholar 

  50. Petrov, K.A., Chauzov, V.A., Bogdanov, N.N., Agafonov, S.V., Zh. Obshch. Khim., 1979, vol. 49, p. 90.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lomonosov Moscow State University, Moscow, 119991, Russia

    N. S. Gulyukina, N. N. Makukhin & I. P. Beletskaya

Authors
  1. N. S. Gulyukina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. N. Makukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. P. Beletskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. S. Gulyukina.

Additional information

Original Russian Text © N.S. Gulyukina, N.N. Makukhin, I.P. Beletskaya, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 633–648.

Beletskaya Irina Petrovna, born in Leningrad. In 1955 graduated from the Chemical Department of the Lomonosov Moscow State University. Candidate of Chemical Sciences since 1958, Doctor of Chemical Sciences since 1963. Professor of Moscow State University since 1970. Correspondent Member of the Academy of Sciences of the USSR (1974), Academician of the Russian Academy of Sciences (1992). Head of the Laboratory of organoelemental compounds of the Chemical Department of Moscow State University. Chief Editor of the Zhurnal Organicheskoi Khimii (Russian Journal of Organic Chemistry), member of the Editorial Boards of a number of Russian and international journals and of the Scientific Councils of the Russian Academy of Sciences. For many years she has been working in IUPAC, has been the President of the Department of organic chemistry (1989–1991). She was awarded the State Prize of the Russian Federation (2004), Lomonosov prize (1979), Mendeleev prize (1982), Nesmeyanov prize (1991), Kapitsa prize (1993), Demidov prize (2003), Arbuzov prize (2007), Balandin prize (2011) etc. Emeritus Academician of the Academy of Sciences of Bashkortostan, honored Professor of Moscow State University, honored professor of Saint-Petersburg State Technological Institute and Cordoba University (Argentina), honored Doctor of Stockholm Royal Technological Institute.

Field of scientific interests: Application of metal complex catalysis to the synthesis of organic and organoelemental compounds, organic catalysis, organic derivatives of lanthanides, carbanions, and nucleophilic aromatic substitution.

Gulyukina Nataliya Sergeevna, born in Moscow. In 1981 graduated from the Chemical Department of the Lomonosov Moscow State University. Candidate of Chemical Sciences since 1988. Assistant Professor of the Chair of organic chemistry of the Chemical Department of the Moscow State University since 2005.

Field of scientific interests: Chemistry of organophosphorus compounds, synthesis of biologically active compounds, stereoselective synthesis, catalytic hydrogenation, metal complex catalysis.

Makukhin Nikolai Nikolaevich, born in 1988 in Akhtubinsk town, Astrakhan oblast. In 2010 graduated from of the Chemical Department of the Lomonosov Moscow State University. Post-graduate student of the Chair of organic chemistry the Chemical Department of the Moscow State University.

Field of scientific interests: Chemistry of small rings, chemistry of organophosphorus compounds, synthesis of biologically active compounds, application of transition metal catalysis in organic synthesis.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gulyukina, N.S., Makukhin, N.N. & Beletskaya, I.P. Synthesis methods of (1-aminocyclopropyl)phosphonic acids. Russ J Org Chem 47, 633–649 (2011). https://doi.org/10.1134/S1070428011050010

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011050010

Keywords

Search

Navigation