An efficient synthesis of 2,3-aziridino-γ-lactones from azetidin-2-ones

Synlett

Volumn , Issue 15, 2005, Pages 2370-2372

  Kale, Ajaykumar S ^a   Deshmukh, Abdul Rakeeb A S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Azetidin 2 ones; Aziridines; Glutamic acid; Lactones

Indexed keywords

AZETIDINE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; LACTONE DERIVATIVE; MESYLIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; ELIMINATION REACTION; SYNTHESIS;

EID: 25644439136     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872263     Document Type: Article

References (42)

1. For reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180.
2. (b) Chemistry and Biology of β-Lactam Antibiotics, Vol. 1-3; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
3. (c) Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993, 621.
4. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
5. The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
6. For comprehensive general reviews, see: (a) Koppel, G. A. In Small Ring Heterocycles, Vol. 42; Hasner, A., Ed.; Wiley: New York, 1983, 219.
7. (b) Backes, J. In Houben-Weyl Methoden der organischem Chemie, Vol. E16B; Muller, E.; Bayer, O., Eds.; Thieme: Stuttgart, 1991, 31.
8. (c) de Kimpe, N. In Comprehensive Heterocyclic Chemistry II, Vol. 1B; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Padwa, A., Eds.; Pergamon: Oxford, 1996, 507.
9. (a) Ojima, I. In The Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993, 197; and references cited therein,
10. (b) Palomo, C.; Aizpurua, J.; Ganboa, I. In Enantioselective Synthesis of Beta-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997, 279; and references cited therein,
11. (c) For a review on this subject see: Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
12. (a) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226.
13. (b) Alcaide, B.; Almendros, P. Synlett 2002, 381.
14. Alcaide, B.; Almendros, P. Curr. Med. Chem. 2004, 11, 1921.
15. Palomo, C.; Aizpurua, J.; Ganboa, I. In Enantioselective Synthesis of Beta-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997, 279-357; and references cited therein.
16. (a) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 1996, 52, 8989.
17. (b) Jayaraman, M.; Puranik, V. G.; Bhawal, B. M. Tetrahedron 1996, 52, 9005.
18. (c) Srirajan, V.; Deshmukh, A. R. A. S.; Puranik, V. G.; Bhawal, B. M. Tetrahedron: Asymmetry 1996, 7, 2733.
19. (d) Krishnaswamy, D.; Govande, V. V.; Deshmukh, A. R. A. S. Synthesis 2003, 1903.
20. (e) Deshmukh, A. R. A. S.; Bhawal, B. M.; Krishnaswamy, D.; Govande, V. V.; Shinkre, B. A.; Jayanthi, A. Curr. Med. Chem. 2004, 11, 1889; and references cited therein,
21. (f) Shirode, N. M.; Kulkarni, K. C.; Gumaste, V. K.; Deshmukh, A. R. A. S. Arkivoc 2005, (i), 53.
22. (a) Yan, Z.; Weaving, R.; Dauban, P.; Dodd, R. H. Tetrahedron Lett. 2002, 43, 7593.
23. (b) Dauban, P.; De Saint-Fuscien, C.; Acher, F.; Prezeau, L.; Barbet, L.; Pin, J.-P.; Dodd, R. H. Bioorg. Med. Chem. Lett. 2000, 10, 129.
24. (c) Dauban, P.; De Saint-Fuscien, C.; Dodd, R. H. Tetrahedron 1999, 55, 7589.
25. (d) Dauban, P.; Chiaroni, A.; Riche, C.; Dodd, R. H. J. Org. Chem. 1996, 61, 2488.
26. (a) Tarrade, A.; Dauban, P.; Dodd, R. H. J. Org. Chem. 2003, 68, 9521; and references cited therein,
27. (b) McCoull, W.; Davis, F. A. Synthesis 2000, 1347; and references cited therein,
28. (c) Dodd, R. H. Molecules 2000, 5, 293; and references cited therein,
29. (d) Dauban, P.; Dubois, L.; Tran Huu Dau, E.; Dodd, R. H. J. Org. Chem. 1995, 60, 2035.
30. (e) Dubois, L.; Mehta, A.; Tourette, E.; Dodd, R. H. J. Org. Chem. 1994, 59, 434.
31. (a) Luisi, R.; Capriati, V.; Florio, S.; Di Cunto, P.; Musio, B. Tetrahedron 2005, 61, 3251.
32. (b) de Saint-Fuscien, C.; Tarrade, A.; Dauban, P.; Dodd, R. H. Tetrahedron Lett. 2000, 41, 6393.
33. (c) Dauban, P.; Hofmann, B.; Dodd, R. H. Tetrahedron 1997, 53, 10743.
34. (d) Dauban, P.; Dodd, R. H. J. Org. Chem. 1997, 62, 4277.
35. (e) Dubois, L.; Dodd, R. H. Tetrahedron 1993, 49, 901.
36. (f) Krutius, O.; Eremeev, A. V.; Sekacis, I. Latv. PSR Zinat. Akad. Vestis, Kim. Ser. 1988, 487,
37. Chem. Abstr. 1989, 110, 114582.
38. (a) Banik, B. K.; Manhas, M. S.; Kaluza, Z.; Barakat, K. J.; Bose, A. K. Tetrahedron Lett. 1992, 33, 3603.
39. (b) Banik, B. K.; Mathur, C.; Wagle, D. R.; Manhas, M. S.; Bose, A. K. Tetrahedron 2000, 56, 5603.
40. Bieg, T.; Szeja, W. Synthesis 1985, 76.
41. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622.
42. 2: C, 69.81; H, 5.86; N, 7.40. Found: C, 69.62; H, 5.43; N, 7.19.