Cobalt π-cations in carbocyclic ring constructions

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9369-9372

  Gill, G Bryon ^a   Pattenden, Gerald ^a   Roan, Graeme A ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599674     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82966-8     Document Type: Article

References (31)

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4. 2. Schrauzer, G. N.; Windgassen, R. J. J. Am. Chem. Soc. 1967, 67, 143; Silverman, R. B.; Dolphin, D.; Babior, B. M. J. Am. Chem. Soc. 1972, 94, 4028 ; Brown, K. L.; Ramamurthy, S.; Marynick, D. S. J. Organomet. Chem. 1985, 287, 377.
5. 2. Schrauzer, G. N.; Windgassen, R. J. J. Am. Chem. Soc. 1967, 67, 143; Silverman, R. B.; Dolphin, D.; Babior, B. M. J. Am. Chem, Soc. 1972, 94, 4028 ; Brown, K. L.; Ramamurthy, S.; Marynick, D. S. J. Organomet. Chem. 1985, 287, 377.
6. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
7. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
8. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
9. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
10. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
11. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
12. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
13. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
14. 3. See for example: Pattenden, G. Chem. Soc. Rev. 1988, 17, 361; Bhandal, H.; Patel, V. F.; Pattenden, G.; Russell, J. J. J. Chem. Soc., Perkin Trans. 1 1990, 2691; Patel, V. F.; Pattenden, G. ibid. 1990, 2703; Bhandal, H.; Howell, A. R.; Patel, V. F.; Pattenden, G. ibid. 1990, 2709; Howell, A. R.; Pattenden, G. ibid 1990, 2715; Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2721; Patel, V. F.; Pattenden, G.; Thompson, D. M. ibid 1990, 2729; Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851; Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369.
15. 4. Ali, A.; Gill, G. B.; Pattenden, G.; Roan, G. A.; Kam, T. S. J. Chem. Soc., Perkin Trans. 1 1996, 1081.
16. 5. Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 379.
17. 6. Begley, M. J.; Cheshire, D. R.; Harrison, T.; Hutchinson, J. M.; Myers, P. L.; Pattenden, G. Tetrahedron 1989, 45, 5215.
18. 7. Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1991, 32, 243.
19. 8. Pattenden, G.; Teague, S. J. Tetrahedron 1987, 43, 5637.
20. 9. Pattenden, G.; Smithies, A. J.; Tapolczay, D.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1 1996, 7; Begley, M. J.; Pattenden, G.; Smithies, A.; Tapolczay, D.; Walter, D .S. ibid 1996, 21; Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. ibid 1996, 31; Batsanov, A.; Chen, L.; Gill, G. B.; Pattenden, G. ibid 1996, 45.
21. 9. Pattenden, G.; Smithies, A. J.; Tapolczay, D.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1 1996, 7; Begley, M. J.; Pattenden, G.; Smithies, A.; Tapolczay, D.; Walter, D .S. ibid 1996, 21; Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. ibid 1996, 31; Batsanov, A.; Chen, L.; Gill, G. B.; Pattenden, G. ibid 1996, 45.
22. 9. Pattenden, G.; Smithies, A. J.; Tapolczay, D.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1 1996, 7; Begley, M. J.; Pattenden, G.; Smithies, A.; Tapolczay, D.; Walter, D .S. ibid 1996, 21; Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. ibid 1996, 31; Batsanov, A.; Chen, L.; Gill, G. B.; Pattenden, G. ibid 1996, 45.
23. 9. Pattenden, G.; Smithies, A. J.; Tapolczay, D.; Walter, D. S. J. Chem. Soc., Perkin Trans. 1 1996, 7; Begley, M. J.; Pattenden, G.; Smithies, A.; Tapolczay, D.; Walter, D .S. ibid 1996, 21; Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. ibid 1996, 31; Batsanov, A.; Chen, L.; Gill, G. B.; Pattenden, G. ibid 1996, 45.
24. 10. For contemporaneous studies see: Gage, J. L.; Branchaud, B. P. J. Org. Chem. 1996, 61, 831.
25. 11. All new compounds showed satisfactory spectroscopic data together with mass spectrometry and/or microanalytical data.
26. 12. Fleming, I.; Paterson, I. Synthesis 1979, 446; Fleming, I.; Marchi, D. Synthesis 1981, 560; Seyferth, D.; Wursthorn, K. R.; Lim, T. F. O.; Sepelak, D. J. J. Organomet. Chem, 1979, 181, 293.
27. 12. Fleming, I.; Paterson, I. Synthesis 1979, 446; Fleming, I.; Marchi, D. Synthesis 1981, 560; Seyferth, D.; Wursthorn, K. R.; Lim, T. F. O.; Sepelak, D. J. J. Organomet. Chem, 1979, 181, 293.
28. 12. Fleming, I.; Paterson, I. Synthesis 1979, 446; Fleming, I.; Marchi, D. Synthesis 1981, 560; Seyferth, D.; Wursthorn, K. R.; Lim, T. F. O.; Sepelak, D. J. J. Organomet. Chem, 1979, 181, 293.
29. 13. Yoshitake, M.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 1991, 2161; Procter, G.; Russell, A. T.; Murphy, P. J.; Tan, T. S.; Mather, A. N. Tetrahedron 1988, 44, 3953.
30. 13. Yoshitake, M.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 1991, 2161; Procter, G.; Russell, A. T.; Murphy, P. J.; Tan, T. S.; Mather, A. N. Tetrahedron 1988, 44, 3953.
31. 14. We presume that the modest yield of 45% reflects the fact that only the major but-3-enyl side chain epimer of 19 undergoes cyclisation to the cis-ring fused perhydroindane 20. The reductive termination of this radical cyclisation reaction, 19→20, was somewhat surprising, but is not unprecedented (see under ref. 3 above).