Organozinc reagents in synthesis: The facile generation of 2-(trialkylsilyl)prop-2-enylzinc from 2-bromo-1-trimethylsilylprop-2-ene

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 2, 1996, Pages 191-199

  Eshelby, James J ^a,b   Parsons, Philip J ^a,c   Crowley, Patrick J ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

^c UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010251186     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000191     Document Type: Article

References (37)

1. B. M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon, Oxford, 1991, vol. 1, ch. 1.
2. (a) E. D. Hughes, C. K. Ingold and G. A. Mair, J. Chem. Soc., 1948, 2072;
3. (b) T. Imamoto, T. Kasumoto, Y. Tawarayama, Y. Sugiura, T. Mita, Y. Hatanaka and M. Yokoyama, J. Org. Chem., 1984, 49, 3904.
4. (a) K. V. Baker, J. M. Brown, N. Hughes, A. J. Skarnulis and A. Sexton, J. Org. Chem., 1991, 56, 698-703;
5. (b) C. Petrier, J. C. de Souza Barbosa, C. Dupuy and J.-L. Luche, J. Org. Chem., 1985, 50, 5761-5765;
6. (c) P. Knochel, M. C. P. Yeh, S. C. Berk and J. Talbert, J. Org. Chem., 1988, 53, 2390;
7. (d) E. Erdik, Tetrahedron, 1987, 43, 2203;
8. (e) R. D. Rieke, Acc. Chem. Res., 1977, 10, 301.
9. H. O. House, W. L. Respess and G. M. Whitesides, J. Org. Chem., 1966, 31, 3128.
10. A. Yanagisawa, K. Yasue and H. Yamamoto, Synlett, 1992, 593.
11. (a) D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc., 1952, 74, 5828;
12. (b) J. W. Cornforth, R. H. Cornforth and K. K. Mathew, J. Chem. Soc., 1959, 112;
13. (c) M. Chérest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 9, 2199;
14. (d) N. T. Anh, Top. Curr. Chem., 1980, 88, 145;
15. (e) M. T. Reetz, Angew. Chem., Int. Ed. Engl., 1984, 23, 1035.
16. (a) I. Fleming and M. Rowley, Tetrahedron, 1989, 45, 413;
17. (b) A. Barbero, P. Cuadrado, A. M. Gonzalez, F. J. Pulido and I. Fleming, J. Chem. Soc., Perkin Trans. 1, 1991, 2811;
18. (c) F. J. Blanco, P. Cuadrado, A. M. Gonzalez, F. J. Pulido and I. Fleming, Tetrahedron Lett., 1994, 35, 8881.
19. L. E. Overman and P. A. Renhowe, J. Org. Chem., 1994, 59, 4138.
20. H. Nishiyama, H. Yokoyama, S. Narimatsu and K. Itoh, Tetrahedron Lett., 1982, 23, 1267.
21. B. M. Trost and B. P. Coppola, J. Am. Chem. Soc., 1982, 104, 3733, 4299, 6879.
22. J. J. Eshelby, P. J. Crowley and P. J. Parsons, Synlett, 1993, 277.
23. J. J. Eshelby, P. J. Crowley and P. J. Parsons, Synlett, 1993, 279.
24. (a) P. Knochel and R. D. Singer, Chem. Rev., 1993, 93, 2117;
25. (b) P. Knochel and J. F. Normant, Tetrahedron Lett., 1984, 25, 4383.
26. (a) H. Achenbach, A. Muhlenfeld, U. Fauth and H. Zahner, Ann. N. Y. Acad. Sci., 1988, 544, 128,
27. (b) H. Nakayama, T. Takatsu, Y. Abe, A. Shimazu, K. Furihata, K. Ikeda, K. Furihata, H. Seto and N. Otake, Agric. Biol. Chem., 1987, 51 (3), 853.
28. M. G. B. Drew, A. Jahans, J. Eshelby and P. J. Parsons, manuscript in preparation.
29. (a) C. H. Behrens, S. Y. Ko, B. Sharpless and F. J. Walker, J. Org. Chem., 1985, 50, 5687;
30. (b) G. B. Payne, J. Org. Chem., 1962, 27, 3819.
31. F. M. Dayrit, D. E. Gladkowski and J. Schwartz, J. Am. Chem. Soc., 1980, 102, 3976.
32. (a) E. Erdik, Tetrahedron, 1992, 48, 9577;
33. (b) E. Negishi, A. O. King and N. Okukado, J. Org. Chem., 1977, 42, 1821.
34. K.-T. Kang, J. C. Lee and J. S. U, Tetrahedron Lett., 1992, 34, 4953.
35. (a) I. Shimizu, K. Hayashi, N. Ide and M. Oshima, Tetrahedron, 1991, 47, (18/19), 2991;
36. (b) R. Sturmer, Liebigs Ann. Chem., 1991, 311;
37. (c) B. E. Rossiter, T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 464.