Generation and reaction of copper(I) hydride in the copper(I) chloride–tributyltin hydride–NMP system: synthesis of 3-norcephalosporin

Abstract

Synthesis of 3-norcephalosporin 1 was performed successfully by reaction of either 3-trifluoromethylsulfonyloxy-Δ³-cephem 2, allenecarboxylate 3 or 3,4-disubstitued but-2-enoates 4 with copper(I) chloride and tributyltin hydride in N-methylpyrrolidin-2-one (NMP). Generation and reactions of a copper(I) hydride species in the copper(I) chloride–tributyltin hydride–NMP or N,N-dimethylformamide (DMF ) system are discussed.

References

1. A. Würtz, Ann. Chim. Phys., 1844, 11, 250.
2. (a) J. A. Dilts and D. F. Shriver, J. Am. Chem. Soc., 1968, 90, 5769; (b) G. M. Whitesides, J. S. Filippo, E. R. Stredronsky and C. P. Casey, J. Am. Chem. Soc., 1969, 91, 6542; (c) J. A. Dilts and D. F. Shriver, J. Am. Chem. Soc., 1969, 91, 4088.
3. (a) S. A. Bezman, M. R. Churchill, J. A. Osborn and J. Wormald, J. Am. Chem. Soc., 1971, 93, 2063; (b) M. R. Churchill, S. A. Bezman, J. A. Osborn and J. Wormald, Inorg. Chem., 1972, 11, 1818; (c) G. V. Goeden and K. G. Caulton, J. Am. Chem. Soc., 1981, 103, 7354; (d) T. H. Lemmen, K. Folting, J. C. Human and K. G. Caulton, J. Am. Chem. Soc., 1985, 107, 7774; (e) D. M. Brestensky, D. E. Huseland, C. McGettigan and J. M. Stryker, Tetrahedron Lett., 1988, 29, 3749; (f) W. S. Mahoney, D. M. Brestensky and J. M. Stryker, J. Am. Chem. Soc., 1988, 110, 291.
4. (a) E. C. Ashby, T. F. Korenowski and R. D. Schwartz, J. Chem. Soc., Chem. Commun., 1974, 157; (b) E. C. Ashby and A. B. Goel, Inorg. Chem., 1977, 16, 3043; (c) E. C. Ashby, J.-J. Lin and A. B. Goel, J. Org. Chem., 1978, 43, 183; (d) D. Masure, P. Coutrot and J. F. Normant, J. Organomet. Chem., 1982, 226, C55.
5. (a) R. K. Boeckman and R. Michalak, J. Am. Chem. Soc., 1974, 96, 1623; (b) S. Masamune, G. S. Bates and P. E. Georghiou, J. Am. Chem. Soc., 1974, 96, 3686.
6. (a) S. Masamune, P. A. Rossy and G. S. Bates, J. Am. Chem. Soc., 1973, 95, 6452; (b) T. Yoshida and E. Negishi, J. Chem. Soc., Chem. Commun., 1974, 762; (c) M. F. Semmelhack and R. D. Stauer, J. Org. Chem., 1975, 40, 3619; (d) M. F. Semmelhack, R. D. Stauer and A. Yamashita, J. Org. Chem., 1977, 42, 3180.
7. B. H. Lipshutz, C. S. Ung and S. Sengupta, Synlett, 1989, 64.
8. S. Ghosal, G. P. Luke and K. S. Kyler, J. Org. Chem., 1987, 52, 4296.
9. (a) E. Piers and T. Wong, J. Org. Chem., 1993, 58, 3609; (b) E. Piers, E. J. McEachern and P. A. Burns, J. Org. Chem., 1995, 60, 2322; (c) E. Piers, E. J. McEachern and M. A. Romero, Tetrahedron Lett., 1996, 37, 1173; (d) E. Piers and M. A. Romero, J. Am. Chem. Soc., 1996, 118, 1215.
10. R. L. Beddoes, T. Cheeseright, J. Wang and P. Quayle, Tetrahedron Lett., 1995, 36, 283.
11. T. Takeda, K. Matsunaga, Y. Kabasawa and T. Fujiwara, Chem. Lett., 1995, 771.
12. G. D. Allred and L. S. Liebeskind, J. Am. Chem. Soc., 1996, 118, 2748.
13. K. C. Nicolaou, M. Sato, N. D. Miller, J. L. Gunzner, J. Renaud and E. Untersteller, Angew. Chem., Int. Ed. Engl., 1996, 35, 889.
14. J. R. Falck, R. K. Bhatt and J. Ye, J. Am. Chem. Soc., 1995, 117, 5973.
15. V. Farina, S. Kapadia, B. Krishnan, C. Wang and L. S. Liebeskind, J. Org. Chem., 1994, 59, 5905 and references cited therein.
16. (a) H. Tanaka, Y. Kameyama, S. Sumida and S. Torii, Tetrahedron Lett., 1992, 33, 7029; (b) H. Tanaka, S. Sumida and S. Torii, Tetrahedron Lett., 1996, 37, 5967.
17. H. Tanaka, Y. Yamaguchi, S. Sumida and S. Torii, Chem. Commun., 1996, 2705.
18. W. Dürckheimier, F. Adam, G. Fischer and R. Kirrstetter, in Advances in Drug Research, ed. B. Testa, Academic Press, New York, 1988, vol. 17, p. 190.
19. N. Asao, J.-X. Liu, T. Sudoh and Y. Yamamoto, J. Org. Chem., 1996, 61, 4568.
20. (a) V. Farina, S. R. Baker and C. Sapino, Tetrahedron Lett., 1988, 29, 6043; (b) S. R. Baker, G. P. Roth and C. Sapino, Synth. Commun., 1990, 20, 2185; (c) V. Farina, S. R. Baker, D. A. Benigni, S. I. Hauck and C. Sapino, J. Org. Chem., 1990, 55, 5833; (d) V. Farina and J. Kant, Synlett, 1994, 565.
21. G. K. Cook, W. J. Hornback, C. L. Jordan, J. H. McDonald and J. E. Munroe, J. Org. Chem., 1989, 54, 5828.
22. (a) J. Kant, C. Sapino and S. R. Baker, Tetrahedron Lett., 1990, 31, 3389; (b) J. Kant, J. Org. Chem., 1993, 58, 2296.
23. V. Farina, S. R. Baker and S. I. Hauck, J. Org. Chem., 1989, 54, 4962.
24. (a) R. L. Elliot, A. K. Takle and J. W. Tyler, J. Org. Chem., 1993, 58, 6954; (b) R. L. Elliot, N. H. Nicholson, F. E. Peaker, A. K. Takle and J. W. Tyler, J. Org. Chem., 1994, 59, 1606.
25. G. Cainelli, M. Contento, M. Panunzio, S. Sandri, A. Umani-Ronchi and M. D. Col, Synlett, 1994, 243.
26. (a) H. Tanaka, Y. Kameyama, S. Sumida, T. Yamada, T. Tokumaru, T. Shiroi, M. Sasaoka, M. Taniguchi and S. Torii, Synlett, 1991, 888; (b) H. Tanaka, S. Sumida, K. Sorajo and S. Torii, J. Chem. Soc., Chem. Commun., 1994, 1461; (c) H. Tanaka, S. Sumida, Y. Kameyama, K. Sorajo, I. Wada and S. Torii, Bull. Chem. Soc. Jpn., 1996, 69, 3651; (d) H. Tanaka, S. Sumida, K. Sorajo, Y. Kameyama and S. Torii, J. Chem. Soc., Perkin Trans. 1, 1997, 637.
27. (a) V. Farina and J. Kant, Tetrahedron Lett., 1992, 33, 3559; (b) J. Kant and V. Farina, Tetrahedron Lett., 1992, 33, 2563; (c) J. Kant, J. A. Roth, C. E. Fuller, D. G. Walker, D. A. Benigni and V. Farina, J. Org. Chem., 1994, 59, 4956; (d) V. Farina and J. Kant, Synlett, 1994, 565.
28. The allenecarboxylate 9 can be stored in a refrigerator for several days without appreciable change but is gradually decomposed under ambient conditions, particularly in the presence of a trace amount of acid or base.
29. H. Tanaka, N. Nishioka, Y. Kameyama, S. Sumida, H. Matsuura and S. Torii, Chem. Lett., 1995, 709.