Indium-mediated facile synthesis of 3-unsubstituted β-lactams

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 14, 2000, Pages 2179-2181

  Banik, Bimal K ^a   Ghatak, Anjan ^a   Becker, Frederick F ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; DECOMPOSITION; ESTERS; INDIUM; SOLVENTS; SYNTHESIS (CHEMICAL);

ALLYLATION; CYCLIZATION;

AROMATIC HYDROCARBONS;

EID: 0034698449     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002833i     Document Type: Article

References (38)

1. For some recent examples, see: (a) A. K. Bose, B. K. Banik, C. Mathur, D. R. Wagle and M. S. Manhas, Tetrahedron, Symposium in Print, 2000, 0000;
2. (b) M. S. Manhas, B. K. Banik, A. Mathur, J. E. Vincent and A. K. Bose, Tetrahedron, Symposium in Print, 2000,0000;
3. (c) A. K. Bose, M. S. Manhas, B. K. Banik and V. Srirajan, in The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Material Science, eds. A. Greenberg, C. M. Breneman and J. F. Liebman, Wiley-Interscience, New York, 2000, p. 157.
4. The usefulness of 3-unsubstituted β-lactams has been documented, see: A. K. Bose, M. S., Manhas, A. Mathur and D. R. Wagle, in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, ed. G. Lukacs, Springer-Verlag, New York, 1993, vol. 2, p. 551.
5. For oxidation reactions: (a) B. K. Banik, A. Ghatak, M. S. Venkatraman and F. F. Becker, Synth. Commun., 2000, 30, 2701;
6. (b) B. K. Banik, A. Ghatak, C. Mukhopadhyay and F. F. Becker, J. Chem. Res. (S), 2000, 108;
7. (c) B. K. Banik, M. S. Venkatraman, C. Mukhopadhyay and F. F. Becker, Tetrahedron Lett., 1998, 39, 7247. For reduction reactions:
8. (d) A. Ghatak, F. F. Becker and B. K. Banik, Tetrahedron Lett., 2000, 41, 3493;
9. (e) B. K. Banik, O. Zegrocka, I. Banik, L. Hackfeld and F. F. Becker, Tetrahedron Lett., 1999, 40, 6731;
10. (f) B. K. Banik, C. Mukhopadhyay, M. S. Venkatraman and F. F. Becker, Tetrahedron Lett., 1998, 39, 7243.
11. B. K. Banik, M. Suhendra, I. Banik and F. F. Becker, Synth. Commun., 2000,0000.
12. Chan and Li have carried out significant work on indium-mediated reactions, for example, see: (a) Y. Yang and T. H. Chan, J. Am. Chem. Soc., 2000, 122, 402;
13. (b) T. H. Chan and Y. Yang, J. Am. Chem. Soc., 1999, 121, 3228;
14. (c) C. J. Li and T. H. Chan, Tetrahedron, 1999, 55, 11149;
15. (d) C. J. Li and T. H. Chan, Organic Reactions in Aqueous Media, J. Wiley & Sons. New York, 1997;
16. (e) C. J. Li, Tetrahedron, 1996, 52, 5643;
17. (f) C. J. Li, Chem. Rev., 1993, 93, 2023;
18. (g) C. J. Li and T. H. Chan, Tetrahedron Lett., 1991, 32, 7017.
19. For various indium-mediated reactions, see: (a) P. K. Choudhury, F. Foubelo and M. Yus, J. Org. Chem., 1999, 64, 3376;
20. (b) P. K. Choudhury, F. Foubelo and M. Yus, Tetrahedron Lett., 1998, 39, 3581;
21. (c) B. C. Ranu, P. Dutta and A. Sarkar, Tetrahedron Lett., 1998, 39, 9557;
22. (d) B. C. Ranu, S. K. Guchhait and A. Sarkar, Chem. Commun., 1998, 2113;
23. (e) C. J. Moody and M. R. Pitts, Synlett 1998, 1028;
24. (f) C. J. Moody and M. R. Pitts, Synlett, 1998, 1029;
25. (g) B. C. Ranu and A. Majee, Chem. Commun., 1997, 1225.
26. For indium-mediated allylation of imines, see: (a) H. A. Hoppe, C. G. Lloyd-Jones, M. Murray, T. M. Peakman and K. E. Walsh, Angew. Chem., Int. Ed., 1998, 37, 1545;
27. (b) S. M. Capps, C. G. Lloyd-Jones, M. Murray, T. M. Peakman and K. E. Walsh, Tetrahedron Lett., 1998, 39, 2853;
28. (c) C. G. Lloyd-Jones and T. Russell, Synlett, 1998, 903;
29. (d) M. Carda, E. Castillo, S. Rodriguez, J. Murga and J. A. Marco, Tetrahedron: Asymmetry, 1998, 9, 1117.
30. (a) L. A. Paquette, R. R. Rothhaar, M. Isaac, L. M. Rogers and R. D. Rogers, J. Org. Chem., 1998, 63, 5463;
31. (b) M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333;
32. (c) M. Jayaraman, M. S. Manhas and A. K. Bose, Tetrahedron Lett., 1997, 38, 709.
33. Grignard-mediated cyclizations of β-amino esters has been reported by several groups. For some examples, see: (a) E. W. Colvin, D. McGarry and M. J. Nugent, Tetrahedron, 1988, 44, 4157;
34. (b) E. J. Thomas and A. C. Williams, J. Chem. Soc., Chem. Commun., 1987, 992.
35. All new compounds described here gave satisfactory spectral data.
36. 4) and con-centrated. Column chromatography over silica gel afforded the β-lactam 2.
37. A. K. Bose, K. Gupta and M. S. Manhas, J. Chem Soc., Chem. Commun., 1984, 86.
38. According to MSDS (Material Safety Data Sheets) obtained from Acros Organics, the toxicological properties of indium have not been fully investigated, but it may be harmful if swallowed