Asymmetric synthesis of 3-amino-β-lactams via staudinger ketene-imine cycloaddition reaction: (Review)

Chemistry of Heterocyclic Compounds

Volumn 34, Issue 11, 1998, Pages 1222-1236

  Palomo, Claudio ^a   Aizpurua, Jesus Maria ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27544459037     PISSN: 00093122     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02256803     Document Type: Review

References (76)

1. (a) W. Durkheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl., 24, 80 (1985).
2. (b) Chemistry and Biology of β-Lactam Antibiotics, R. B. Morin and M. Gorman (eds.), Academic Press, New York, Vol. 1-3 (1982).
3. (c) 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).
4. (d) R. Southgate, Contemp. Org. Synth., 1, 417 (1994).
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).
6. The Chemistry of β-Lactams, M. I. Page (ed.), Chapman and Hall, London (1992).
7. (a) G. A. Koppel in: Small Ring Heterocycles, A. Hassner (ed.), Wiley, New York, 42, 219 (1983).
8. (b) J. Backes in: Houben-Weyl, Methoden der Organischen Chemie, Band E16B. E. Muller and O. Bayer (eds.), Thieme, Stuttgart (1991), p. 31.
9. (c) N. DeKimpe in: Comprehensive Heterocyclic Chemistry II, A. Padwa (ed.), 1B, 507 (1996).
10. M. J. Miller, Acc. Chem. Res., 28, 299 (1995).
11. (a) D. J. Hart and D. C. Ha, Chem. Rev., 89, 1447 (1989).
12. (b) M. J. Brown, Heterocycles, 29, 2225 (1989).
13. (c) G. I. Georg in: Natural Product Chemistry, A.-ur. Rahman (ed.), Elsevier, Amsterdam, 4, 431 (1989).
14. (d) T. Fujisawa and M. Shimizu, Rev. Heteroatom. Chem., 15, 203 (1996).
15. (e) G. Cainelli, M. Panunzio, P. Andreoli, G. Martelli, G. Spunta, D. Giacomini, and E. Bandini, Pure Appl. Chem., 62, 605 (1990).
16. (f) 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.
17. (a) L. S. Hegedus, Acc. Chem. Res., 28, 299 (1995).
18. (b) M. A. Barrett and M. A. Stutgess, Tetrahedron, 44, 5615 (1988).
19. H. Staudinger, Liebigs Ann. Chem., Bd 356, S. 51 (1907).
20. F. H. Van der Steen and G. Van Koten, Tetrahedron, 47, 7503 (1991).
21. (a) R. C. Thomas, in: Recent Progress in The Chemical Synthesis of Antibiotics, G. Lukacs and M. Ohno (eds.), Springer-Verlag, Berlin (1990), p. 533.
22. (b) 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.
23. (c) L. Ghosez and J. Marchand-Brynaert, in: Comprehensive Organic Synthesis, B. Trost and I. Fleming (eds.), Pergamon, Oxford, 5, 85 (1991).
24. (a) R. D. G. Cooper, B. W. Daugherty, and D. B. Boyd, Pure Appl. Chem., 59, 485 (1987).
25. (b) F. H. Van der Steen and G. Van Koten, Tetrahedron, 47, 5703 (1991).
26. (c) G. I. Georg and V. T. Ravikumar, in: The Organic Chemistry of β-Lactams, G. I. Georg (ed.), WCH, New York (1993), p. 295.
27. A. K. Bose, M. S. Manhas, J. M. van der Veen, S. S. Bari, and D. R. Wagle, Tetrahedron, 48, 4831 (1992).
28. T. E. Gunda and F. Sztaricskai, Tetrahedron, 53, 7985 (1997).
29. G. I. Georg and Z. Wu, Tetrahedron Lett., 35, 381 (1991).
30. (a) C. Hubschwerlen and G. Schmid, Helv. Chim. Acta, 66, 2206 (1983).
31. (b) 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).
32. (c) B. K. Banik, M. S. Manhas, Z. Kaluza, J. K. Barakat, and A. K. Bose, Tetrahedron Lett., 33, 3603 (1992).
33. (d) 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).
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).
36. (a) M. Jayaraman, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron, 52, 8989 (1996).
37. (b) M. Jayaraman, V. G. Puranik, and B. M. Bhawal, Tetrahedron, 52, 9005 (1996).
38. C. Palomo, F. P. Cossio, C. Cuevas, J. M. Ontoria, J. M. Odriozola, and S. Munt, Bull. Soc. Chim. Belg., 101, 541 (1992).
39. M. Jayaraman, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron, 52, 3741 (1996).
40. (a) D. A. Evans and E. B. Sjogren, Tetrahedron Lett., 27, 3783 (1985).
41. (b) D. L. Boger, J. B. Myers, Jr., J. Org. Chem., 56, 5385 (1991).
42. (c) M. Muller, D. Bur, T. Tschamber, and J. Streith, Helv. Chim. Acta, 74, 767 (1991).
43. I. Ojima, Chem. Res., 28, 383 (1995).
44. C. Palomo, J. M. Aizpurua, J. I. Miranda, A. Mielgo, and J. M. Odriozola, Tetrahedron Lett., 34, 6325 (1993).
45. R. A. Holton and J. H. Liu, Bioorg, Med. Chem. Lett., 3, 2475 (1993).
46. V. Srirajan, V. G. Puranik, A. R. A. S. Deshmukh, and B. M. Bhawal, Tetrahedron, 52, 5579 (1996).
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).
48. C. Palomo, J. M. Aizpurua, A. Mielgo, and R. Galarza, Chem. Eur. J., 3, 1432 (1997).
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).
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).
52. B. Alcaide, Y. Martin-Cantalejo, J. Perez-Castells, M. A. Sierra, and A. Monge, J. Org. Chem., 61, 9156 (1996).
53. C. Niu, T. Petterson and M. J. Miller, J. Org. Chem., 61, 1014 (1996).
54. C. Palomo, J. M. Aizpurua, A. Mielgo, and A. Linden, J. Org. Chem., 61, 9186 (1996).
55. E. Bindini, G. Martelli, G. Spunta, and M. Panunzio, Synlett., 1017 (1997).
56. R. D. G. Cooper, in ref. 3, 7985.
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).
58. J. Kant and D. G. Walker, in: The Organic Chemistry of β-Lactams, G. I. Georg (ed.), VCH, New York (1993), p. 121.
59. (a) M. Hatanaka and T. Ishimaru, Tetrahedron Lett., 24, 4837 (1983).
60. (b) B. G. Jackson, J. P. Gardner, and P. C. Heath, Tetrahedron Lett., 31, 6317 (1990).
61. (c) M. J. Zmijewski, B. S. Briggs, A. R. Thompson, and I. G. Wright, Tetrahedron Lett., 32, 1621 (1991).
62. (d) C. W. Doecke, M. A. Staszak, and W. D. Luke, Synlett., 985 (1991).
63. (e) J. W. Frazier, M. A. Staszak, and L. O. Weigel, Tetrahedron Lett., 33, 857 (1992).
64. (f) P. R. Guzzo and M. J. Miller, J. Org. Chem., 59, 4862 (1994).
65. (a) D. A. Evans, E. B. Sjogren, Tetrahedron Lett., 26, 3787 (1985).
66. (b) 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).
67. (c) C. Bodurow and M. A. Carr, Tetrahedron Lett., 30, 4081 (1989).
68. (d) R. K. Vaid and T. E. Hopkins, Tetrahedron Lett., 38, 6981 (1997).
69. (a) S. Oumoch and G. Rousseau, Heterocycles, 43, 2615 (1997).
70. (b) S. Oumoch and G. Rousseau, Bull. Soc. Chim. Fr., 133, 997 (1996).
71. (c) M. G. Stocksdale, S. Ramurthy, and M. J. Miller, J. Org. Chem., 63, 1221 (1998).
72. T. Fujisawa and M. Shimizu, Jpn. Kokai Tokkyo Koho JP 07,300,490 [95,300,490] (1995); Chem. Abstr., 124, 260700d (1996).
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).
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.