Participation of sulphonamide nitrogen in the rearrangement of the 2-azabicyclo[2.2.2]octane skeleton: An efficient synthesis of the 6-azabicyclo[3.2.1]octan-4-one system

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 24, 1983, Pages 1490-1492

  Holmes, Andrew B ^a   Raithby, Paul R ^a   Thompson, John ^a   Baxter, Andrew J G ^b   Dixon, John ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049112822     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/c39830001490     Document Type: Article

References (21)

1. A. J. G. Baxter and A. B. Holmes, J. Chem. Soc., Perkin Trans. 1, 1977, 2343.
2. R. Albrecht and G. Kresze, Chem. Ber., 1965, 98, 1431.
3. J. M. Hook, Synth. Commun., in the press.
4. G. R. Krow and D. M. Fan, J. Org. Chem., 1974, 39, 2674.
5. G. R. Krow and D. A. Shaw, Synth. Commun., 1982, 12, 313.
6. R. O. Hutchins and L. Rua, J. Org. Chem., 1975, 40, 2567.
7. W. Nagata, S. Hirai, K. Kawata, and T. Okumura, J. Am. Chem. Soc., 1967, 89, 5046.
8. G. R. Krow, D. A. Shaw, C. S. Jovais, and H. G. Ramjit, Synth. Commun., 1983, 13, 575.
9. L. A. Paquette and J. F. Kelly, J. Org. Chem., 1971, 36, 442.
10. A. Bowers, T. G. Halsall, E. R. H. Jones, and A. J. Lemin, J. Chem. Soc., 1953, 2548.
11. H. E. Zimmerman and A. Mais, J. Am. Chem. Soc., 1959, 81, 3644.
12. H. O. House, ‘Modern Synthetic Reactions,’ 2nd edn., W. A. Benjamin, Menlo Park, California, 1972, p. 218.
13. D. P. G. Hamon and R. W. Sinclair, Chem. Commun., 1968, 890.
14. W. M. Dadson and T. Money, Can. J. Chem., 1980, 58, 2524.
15. H. G. Kuivila, Synthesis, 1970, 499.
16. W. A. M. Davies, A. R. Pinder, and I. G. Morris, Tetrahedron, 1962, 18, 405.
17. J. W. Huffman, T. Kamiya, and B. B. S. Rao, J. Org. Chem., 1967, 32, 700.
18. R. A. Perry, S. C. Chen, B. C. Menon, K. Hanaya, and Y. L. Chow, Can. J. Chem., 1976, 54, 2385.
19. G. R. Krow, K. M. Damodaran, D. M. Fan, R. Rodebaugh, A. Gaspari, and U. K. Nadir, J. Org. Chem., 1977, 42, 2486.
20. J. Lacrampe, A. Heumann, R. Furstoss, and B. Waegell, J. Chem. Res., 1978, (S) 334.
21. J. Lacrampe, A. Heumann, R. Furstoss, and B. Waegell, J. Chem. Res., 1978, (M) 4001, and references cited.