Skip to main content
SpringerLink
Log in

Asymmetric synthesis of 3-amino-β-lactamsvia Staudinger ketene-imine cycloaddition reaction (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Recent advances in asymmetric synthesis of 3-amino-β-lactamsvia Staudinger ketene-imine cycloaddition reaction are summarized.

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.

Similar content being viewed by others

References

  1. W. Durkheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl.,24, 80 (1985).

    Google Scholar 

  2. Chemistry and Biology of β-Lactam Antibiotics, R. B. Morin and M. Gorman (eds.), Academic Press, New York, Vol. 1–3 (1982).

    Google Scholar 

  3. R. Southgate, C. Branch, S. Coulton, and E. Hunt, in: Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, G. Lukacs (ed.), Springer-Verlag, Berlin,2, 621 (1993).

    Google Scholar 

  4. R. Southgate, Contemp. Org. Synth.,1, 417 (1994).

    Google Scholar 

  5. R. Southgate, S. Elson, in: The Chemistry of Organic Natural Products, W. Herz H. Grisebach, G. W. Kirby, and Ch. Tamm (eds.), Springer-Verlag, Wien,47, 1 (1985).

    Google Scholar 

  6. The Chemistry of β-Lactams, M. I. Page (ed.), Chapman and Hall, London (1992).

    Google Scholar 

  7. G. A. Koppel in: Small Ring Heterocycles, A. Hassner (ed.), Wiley, New York,42, 219 (1983).

    Google Scholar 

  8. J. Backes in: Houben-Weyl, Methoden der Organischen Chemie, Band E16B. E. Muller and O. Bayer (eds.), Thieme, Stuttgart (1991), p. 31.

    Google Scholar 

  9. N. DeKimpe in: Comprehensive Heterocyclic Chemistry, II, A. Padwa (ed.),1B, 507 (1996).

  10. M. J. Miller, Acc. Chem. Res.,28, 299 (1995).

    Google Scholar 

  11. D. J. Hart and D. C. Ha, Chem. Rev.,89, 1447 (1989).

    Google Scholar 

  12. M. J. Brown, Heterocycles,29, 2225 (1989).

    Google Scholar 

  13. G. I. Georg in: Natural Product Chemistry, A.-ur. Rahman (ed.), Elsevier, Amsterdam,4, 431 (1989).

    Google Scholar 

  14. T. Fujisawa and M. Shimizu, Rev. Heteroatom. Chem.,15, 203 (1996).

    Google Scholar 

  15. G. Cainelli, M. Panunzio, P. Andreoli, G. Martelli, G. Spunta, D. Giacomini, and E. Bandini, Pure Appl. Chem.,62, 605 (1990).

    Google Scholar 

  16. G. Cainelli, M. Panunzio, D. Giacomini, G. Martelli, G. Spunta, and E. Bandini, in: Chemical Synthesis, Gnosis to Prognosis, C. Chatgilialoglu and V. Snieckus (eds.), Kluwer Academic, Amsterdam (1996), p. 25.

    Google Scholar 

  17. L. S. Hegedus, Acc. Chem. Res.,28, 299 (1995).

    Google Scholar 

  18. M. A. Barrett and M. A. Stutgess, Tetrahedron,44, 5615 (1988).

    Google Scholar 

  19. H. Staudinger, Liebigs Ann. Chem., Bd 356, S. 51 (1907).

    Google Scholar 

  20. F. H. Van der Steen and G. Van Koten, Tetrahedron,47, 7503 (1991).

    Google Scholar 

  21. R. C. Thomas, in: Recent Progress in The Chemical Synthesis of Antibiotics, G. Lukacs and M. Ohno (eds.), Springer-Verlag, Berlin (1990), p. 533.

    Google Scholar 

  22. R. J. Ternansky and J. M. Morin, Jr., in: The Organic Chemistry of β-Lactams, G. I. Georg (ed.), WCH, New York (1993), p. 257.

    Google Scholar 

  23. L. Ghosez and J. Marchand-Brynaert in: Comprehensive Organic Synthesis, B. Trost and I. Fleming (eds.), Pergamon, Oxford,5, 85 (1991).

    Google Scholar 

  24. R. D. G. Cooper, B. W. Daugherty, and D. B. Boyd, Pure Appl. Chem.,59, 485 (1987).

    Google Scholar 

  25. F. H. Van der Steen, and G. Van Koten, Tetrahedron,47, 5703 (1991).

    Google Scholar 

  26. G. I. Georg and V. T. Ravikumar, in: The Organic Chemistry of β-Lactams, G. I. Georg (ed.), WCH, New York (1993), p. 295.

    Google Scholar 

  27. A. K. Bose, M. S. Manhas, J. M. van der Veen, S. S. Bari, and D. R. Wagle, Tetrahedron,48, 4831 (1992).

    Google Scholar 

  28. T. E. Gunda and F. Sztaricskai, Tetrahedron,53, 7985 (1997).

    Google Scholar 

  29. G. I. Georg and Z. Wu, Tetrahedron Lett.,35, 381 (1991).

    Google Scholar 

  30. C. Hubschwerlen and G. Schmid, Helv. Chim. Acta,66, 2206 (1983).

    Google Scholar 

  31. D. R. Wagle, G. Garai, J. Chiang, M. G. Monteleone, B. E. Kurys, T. W. Strohmeyer, V. R. Hedge, M. S. Manhas, and A. K. Bose, J. Org. Chem.,53, 4227 (1988).

    Google Scholar 

  32. B. K. Banik, M. S. Manhas, Z. Kaluza, J. K. Barakat, and A. K. Bose, Tetrahedron Lett.,33, 3603 (1992).

    Google Scholar 

  33. C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. Y. Miranda, and A. Linden, J. Org. Chem., and references therein (1998).

  34. E. Bandini, G. Martelli, G. Spunta, A. Bongini, and M. Panunzio, Tetrahedron Lett.37, 4409 (1996).

    Google Scholar 

  35. C. Palomo, F. P. Cossio, C. Cuevas, B. Lecea, A. Mielgo, P. Roman, A. Luque, and M. Martinez-Ripoll, J. Am. Chem. Soc.,114, 9360 (1992).

    Google Scholar 

  36. M. Jayaraman, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron52, 8989 (1996).

    Google Scholar 

  37. M. Jayaraman, V. G. Puranik, and B. M. Bhawal, Tetrahedron,52, 9005 (1996).

    Google Scholar 

  38. C. Palomo, F. P. Cossio, C. Cuevas, J. M. Ontoria, J. M. Odriozola, and S. Munt, Bull. Soc. Chim. Belg.,101, 541 (1992).

    Google Scholar 

  39. M. Jayaraman, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron,52, 3741 (1996).

    Google Scholar 

  40. D. A. Evans and E. B. Sjogren, Tetrahedron Lett.,27, 3783 (1985).

    Google Scholar 

  41. D. L. Boger, J. B. Myers, Jr., J. Org. Chem.,56, 5385 (1991).

    Google Scholar 

  42. M. Muller, D. Bur, T. Tschamber, and J. Streith, Helv. Chim. Acta,74, 767 (1991).

    Google Scholar 

  43. I. Ojima, Chem. Res.,28, 383 (1995).

    Google Scholar 

  44. C. Palomo, J. M. Aizpurua, J. I. Miranda, A. Mielgo, and J. M. Odriozola, Tetrahedron Lett.,34, 6325 (1993).

    Google Scholar 

  45. R. A. Holton and J. H. Liu, Bioorg, Med. Chem. Lett.,3, 2475 (1993).

    Google Scholar 

  46. V. Srirajan, V. G. Puranik, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron,52, 5579 (1996).

    Google Scholar 

  47. C. Palomo, J. M. Aizpurua, M. Legido, R. Galarza, P. M. Deya, J. Dunogues, J. P. Picard, A. Ricci, and G. Seconi, Angew. Chem. Int. Ed. Engl.,35, 1239 (1996).

    Google Scholar 

  48. C. Palomo, J. M. Aizpurua, A. Mielgo, and R. Galarza, Chem. Eur. J.,3, 1432 (1997).

    Google Scholar 

  49. C. Palomo, J. M. Aizpurua, M. Legido, and R. Galarza, Chem. Commun., 233 (1997).

  50. C. Palomo, J. M. Aizpurua, J. M. Garcia, R. Galarza, M. Legido, R. Urchegui, P. Roman, A. Luque, J. Server-Carrio, and A. Linden, J. Org. Chem.,62, 2070 (1997).

    Google Scholar 

  51. B. Alcaide, Y. Martin-Cantalejo, J. Perez-Castells, J. Rodriguez-Lopez, M. A. Sierra, A. Monge, and V. Perez-Garcia, J. Org. Chem.,57, 5921 (1992).

    Google Scholar 

  52. B. Alcaide, Y. Martin-Cantalejo, J. Perez-Castells, M. A. Sierra, and A. Monge, J. Org. Chem.,61, 9156 (1996).

    Google Scholar 

  53. C. Niu, T. Petterson and M. J. Miller, J. Org. Chem.,61, 1014 (1996).

    Google Scholar 

  54. C. Palomo, J. M. Aizpurua, A. Mielgo, and A. Linden, J. Org. Chem.,61, 9186 (1996).

    Google Scholar 

  55. E. Bindini, G. Martelli, G. Spunta, and M. Panunzio, Synlett., 1017 (1997).

  56. R. D. G. Cooper, in ref. 3, Chapman and Hall, London (1983), 7985.

    Google Scholar 

  57. J. B. Deeter, D. A. Hall, C. L. Jordan, R. M. Justice, M. D. Kinnick, J. M. Morin, Jr., J. W. Paschal, and R. J. Ternansky, Tetrahedron Lett.,34, 3051 (1993).

    Google Scholar 

  58. J. Kant and D. G. Walker, in: The Organic Chemistry of β-Lactams, G. I. Georg (ed.), VCH New York (1993), p. 121.

    Google Scholar 

  59. M. Hatanaka and T. Ishimaru, Tetrahedron Lett.,24, 4837 (1983).

    Google Scholar 

  60. B. G. Jackson, J. P. Gardner, and P. C. Heath, Tetrahedron Lett.,31, 6317 (1990).

    Google Scholar 

  61. M. J. Zmijewski, B. S. Briggs, A. R. Thompson, and I. G. Wright, Tetrahedron Lett.,32, 1621 (1991).

    Google Scholar 

  62. C. W. Doecke, M. A. Staszak, and W. D. Luke, Synlett. 985 (1991).

  63. J. W. Frazier, M. A. Staszak, and L. O. Weigel, Tetrahedron Lett.,33, 857 (1992).

    Google Scholar 

  64. P. R. Guzzo and M. J. Miller, J. Org. Chem.,59, 4862 (1994).

    Google Scholar 

  65. D. A. Evans, E. B. Sjogren, Tetrahedron Lett.,26, 3787 (1985).

    Google Scholar 

  66. C. C. Bodurow, B. D. Boyer, J. Brennan, C. A. Bunnell J. E. Burks, M. A. Carr, C. W. Doecke, T. M. Eckrich, J. W. Fischer, J. P. Gardner, B. J. Graves, R. C. Hines, P. Hoying, B. G. Jackson, M. D. Kinnick, C. D. Kochert, J. S. Lewis, W. D. Luke, L. L. Moore, J. M. Morin, Jr., R. L. Nist, D. E. Prather, D. L. Sparks, and W. C. Vladuchick, Tetrahedron,30, 2321 (1989).

    Google Scholar 

  67. C. Bodurow and M. A. Carr, Tetrahedron Lett.,30, 4081 (1989).

    Google Scholar 

  68. R. K. Vaid and T. E. Hopkins, Tetrahedron Lett.,38, 6981 (1997).

    Google Scholar 

  69. S. Oumoch and G. Rousseau, Heterocycles,43, 2615 (1997).

    Google Scholar 

  70. S. Oumoch and G. Rousseau, Bull. Soc. Chim. Fr.,133, 997 (1996).

    Google Scholar 

  71. M. G. Stocksdale, S. Ramurthy, and M. J. Miller, J. Org. Chem.,63, 1221 (1998).

    Google Scholar 

  72. T. Fujisawa and M. Shimizu, Jpn. Kokai Tokkyo Koho JP 07,300,490 [95,300,490], (1995); Chem. Abstr.,124, 260700d (1996).

    Google Scholar 

  73. T. Fujisawa, A. Shibuya, D. Sato, and M. Shimizu, Synlett., 1067 (1995).

  74. J. W. Fischer, J. M. Dunigan, L. D. Hatfield, R. C. Hoying, J. E. Ray, and K. L. Thomas, Tetrahedron Lett.,34, 4755 (1993).

    Google Scholar 

  75. C. Palomo, I. Ganboa, A. Kot, and L. Dembkowski, J. Org. Chem., 199 (in press).

  76. C. Palomo, J. M. Aizpurua, and I. Ganboa, in: Enantioselective Synthesis of α-Amino Acids. E. Juaristi (ed.), Wiley-VCH, New York (1997), p. 279.

    Google Scholar 

Download references

Authors
  1. Claudio Palomo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jesus Maria Aizpurua
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Departamento de Quimica Organica, Universidad del Pais Vasco. Facultad de Quimica, Apdo. 1072, 20080 San Sebastian, Spain. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1448–1462, November, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Palomo, C., Aizpurua, J.M. Asymmetric synthesis of 3-amino-β-lactamsvia Staudinger ketene-imine cycloaddition reaction (review). Chem Heterocycl Compd 34, 1222–1236 (1998). https://doi.org/10.1007/BF02256803

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02256803

Keywords

Search

Navigation