Rapid entry to enantiopure carbacepham derivatives via Lewis acid promoted carbonyl-ene cyclization of 2-azetidinone-tethered alkenylaldehydes

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4205-4208

  Alcaide, Benito ^a   Pardo, Carmen ^a   Rodríguez Ranera, Carolina ^a   Rodríguez Vicente, Alberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

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EID: 0000379088     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016871a     Document Type: Article

References (31)

1. For reviews, see: (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
2. (b) Snider, B. B. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 527.
3. (c) Snieckus, V.; Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 476.
4. See. for example: (a) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333.
5. (b) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
6. (c) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 621.
7. (d) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992A.
8. See, for instance: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321.
9. (b) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
10. (c) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
11. Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226 and references therein.
12. Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
13. To the best of our knowledge there is only one example of ene reaction for the synthesis of a cepham derivative via a transient sulfinyl cation: Kokulja, S.; Lammert, S. R.; Gleissner, M. R. B.; Ellis, A. I. J. Am. Chem. Soc. 1976, 98, 5040.
14. Carbacephems are a promising new family of β-lactam antibiotics closely related to the widely used cephalosporins, with similar antibacterial profiles but with greater chemical stability and enhanced pharmacokinetic properties. See, for example: (a) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8, p 272. See, also:
15. (b) Folmer, J. J.; Acero, C.; Thai, D. L.; Rapoport, H. J. Org. Chem. 1998, 63, 8170.
16. (c) Palomo, C.; Ganboa, I.; Kot, A.; Dembkowski, L. J. Org. Chem. 1998, 63, 6398.
17. (d) Ciufulini, M. A. Chem. Commun. 1996, 881.
18. (e) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618.
19. (a) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Mannas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227.
20. (b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry-of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 295.
21. See, for example: (a) Alcaide, B.; Almendros, P.; R.-Salgado, N. J. Org. Chem. 2000, 65, 3310.
22. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612.
23. 4, and the solvent was removed under reduced pressure. After purification by flash chromatography, carbacepham 2a was obtained in analytically pure form.
24. 3: C, 70.31; H, 7.01; N, 5.12. Found; C, 70.50; H, 7.21; N, 5.08.
25. Andersen, N. H.; Hadley, S. W.; Kelly, J. D.; Bacon, E. R. J. Org. Chem. 1985, 50, 4144.
26. Alcaide, B.; Almendros, P.; R.-Salgado, N.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Eur. J. Org. Chem. 2001, 2001.
27. The poor selectivity obtained in allylation of compound 8 is in clear contrast with the excellent stereoselectivity observed by Ojima for related type 2 alkylations in chiral 4-phenyl-β-lactam acetates. See, for example: Ojima, I.; Komata, T.; Qiu, X. J. Am. Chem. Soc. 1990, 112, 770.
28. For models on the carbonyl-ene cyclization reaction, see: (a) Braddock, D. Ch.; Hu, K. K.; Brown, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 1720.
29. (b) Mikami, K.; Sawa, E.; Terada, M. Tetrahedron: Asymmetry 1991, 2, 1403.
30. (c) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 9011.
31. (d) Johnston, M.; Kwass, J. A.; Beal, R. B.; Snider, B. B. J. Org. Chem. 1987, 52, 5419.