The conjugate addition of a silyl group to enones and its removal with copper(II) bromide: A protecting group for the αβ-unsaturation of αβ-unsaturated ketones

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1981, Pages 2520-2526

  Ager, David J ^a   Fleming, Ian ^a   Patel, Shailesh K ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049109266     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19810002520     Document Type: Article

References (32)

1. I. Fleming and J. Goldhill, J. Chem. Soc., Perkin Trans. 1, 1980, 1493.
2. D. Ager and I. Fleming, J. Chem. Soc., Chem. Commun., 1978, 177.
3. W. C. Still, J. Org. Chem., 1976, 41, 3063.
4. W. C. Still and A. Mitra, Tetrahedron Lett., 1978, 2659.
5. R. Calas and J. Dunoguès, Organometal. Chem. Rev., 1976, 2, 277.
6. E. Hengge and N. Holtschmidt, J. Organomet. Chem., 1968, 12, P5.
7. E. Wiberg, O. Stecher, H. J. Andrascheck, L. Krewbichler, and E. Staude, Angew. Chem., Int. Edn. Engl., 1963, 2, 507.
8. H. Gilman and G. D. Lichten waiter, J. Am. Chem. Soc., 1958, 80, 608.
9. L. C. King and G. K. Ostrum, J. Org. Chem., 1964, 29, 2459.
10. E. Warnhoff, M. Rampersad, P. Sundara Raman, and F. W. Yerhoff, Tetrahedron Lett., 1978, 1659.
11. N. Inukai, H. Iwamoto, T. Tamura, I. Yanagisawa, Y. Ishii, and M. Murakami, Chem. Pharm. Bull., 1976, 24, 820.
12. M. E. C. Biffin, A. G. Moritz, and D. B. Paul, Aust. J. Chem., 1972, 25, 1329.
13. G. H. Posner, ‘An Introduction to Synthesis Using Organocopper Reagents,’ Wiley, New York, 1980.
14. A. Marquet and J. Jacques, Bull. Soc. Chim. Fr., 1962, 90.
15. R. E. Ellison, Synthesis, 1973, 397.
16. T.-L. Ho, Synth. Commun., 1974, 265.
17. T.-L. Ho, Synth. Commun., 1977, 7, 351.
18. T.-L. Ho, Synth. Commun., 1981, 11, 7.
19. M. A. Guaciaro, P. M. Wovkulich, and A. B. Smith, Tetrahedron Lett., 1978, 4661.
20. For example, see T. C. Jain, C. M. Banks, and J. E. McCloskey, Tetrahedron, 1976, 32, 765.
21. Y. Nagao, K. Kaneko, and E. Fujita, Tetrahedron Lett., 1976, 1215.
22. A. Itoh, S. Ozawa, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1980, 361.
23. M. W. Cronyn and G. H. Reisser, J. Am. Chem. Soc., 1953, 75, 1664.
24. J. Dunoguès, A. Ekouya, R. Calas, and N. Duffaut, J. Organomet. Chem., 1975, 87, 151.
25. K. A. Andrianov and N. V. Delazari, Dokl. Akad. Nauk SSSR, 1958, 122, 393.
26. K. A. Andrianov and N. V. Delazari, Chem. Abs., 1959, 53, 2133.
27. G. M. Whitesides, C. P. Casey, and J. K. Krieger, J. Am. Chem. Soc., 1971, 93, 1379.
28. G. M. Whitesides, C. P. Casey, and J. K. Krieger, ‘Handbook of Physics and Chemistry,’ Chemical Rubber Company, Cleveland, Ohio, 47th edn., 1966.
29. G. M. Whitesides, C. P. Casey, and J. K. Krieger, ‘Dictionary of Organic Compounds,’ Eyre and Spottiswoode, London, 4th edn., 1965.
30. R. E. Ireland, D. A. Evans, D. Glover, G. M. Rubottom, and H. Young, J. Org. Chem., 1969, 34, 3717.
31. T. Mukaiyama, K. Banno, and K. Narasaka, J. Am. Chem. Soc., 1974, 96, 7503.
32. I. Paterson and I. Fleming, Tetrahedron Lett., 1979, 2179.