Facile Preparation of Vicinal Allylsiloxy- and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 9, 1997, Pages 2255-2263

  Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001569781     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.2255     Document Type: Article

References (38)

1. a) D. P. Curran, "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 4, pp. 779-831;
2. b) A. L. Beckwith, Tetrahedron, 37, 3073 (1981);
3. c) B. Giese, "Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds," Pergamon Press, Oxford (1986), pp. 141-209;
4. d) D. J. Hart, Science, 223, 883 (1984);
5. e) G. Stork, Bull. Chem. Soc. Jpn., 61, 149 (1988);
6. f) D. P. Curran, Synthesis, 1988, 417;
7. g) D. P. Curran, Synlett, 1991, 63.
8. a) H. Nishiyama, T. Kitajima, M. Matsumoto, and K. Ito, J. Org. Chem., 49, 2298 (1984);
9. b) G. Stork and M. Kahn, J. Am. Chem. Soc., 107, 500 (1985);
10. c) J. W. Wilt, Tetrahedron, 41, 3979 (1985);
11. d) G. Stork and M. J. Sofia, J. Am. Chem. Soc., 108, 6826 (1986);
12. e) M. Koreeda and I. A. George, J. Am. Chem. Soc., 108, 8098 (1986);
13. f) K. Tamao, K. Maeda, and Y. Ito, J. Am. Chem. Soc., 111, 4984 (1989);
14. g) M. Koreeda and L. G. Hamann, J. Am. Chem. Soc., 112, 8175 (1990);
15. h) M. Journet and M. Malacria, J. Org. Chem., 57, 3085 (1992);
16. i) K. Tamao, K. Nagato, Y. Ito, K. Maeda, and M. Shiro, Synlett, 1994, 254;
17. j) E. Magnol and M. Malacria, Tetrahedron Lett., 27, 2255 (1986).
18. a) I. Fleming, Chemtracts. Org. Chem., 9, 1 (1996);
19. b) K. Tamao, N. Ishida, and M. Kumada, J. Org. Chem., 48, 2120 (1983);
20. c) K. Tamao, T. Kakui, M. Akita, T. Iwahara, R. Kanatani, J. Yoshida, and M. Kumada, Tetrahedron, 39, 983 (1983).
21. D. P. Curran and P. S. Ramamoorthy, Tetrahedron, 49, 4841 (1993).
22. H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron, 52, 503 (1996).
23. H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 34, 1951 (1993); H. Shinokubo, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron, 52, 503 (1996).
24. H. Shinokubo, K. Oshima, and K. Utimoto, Chem. Lett., 1995, 461.
25. (Allyldimethylsilyl)dibromomethane or (vinyldimethylsilyl)dibromomethane was easily prepared by an addition of lithium diisopropylamide to a mixture of dibromomethane and the corresponding allyl- or vinyl-substituted chlorosilane at -78 °C. See Ref. 5.
26. K. Takaku, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 37, 6781 (1996).
27. Treatment of allyl alcohol with butyl vinyl ether in the presence of NIS at -78 °C for 1 h afforded 1-allyloxy-1-butoxy-2iodoethane (20) in 96% yield.
28. Allyl(diphenyl)silanol was obtained in 85% yield by an addition of allylmagnesium chloride to a solution of dichlorodiphenylsilane in THF at -78 °C followed by hydrolytic workup. Vinyl(diphenyl)silanol was easily prepared from commercially available chlorodiphenylvinylsilane by hydrolysis with 1 M aqueous sodium hydroxide in ether at 0 °C in 95% yield.
29. K. Miura, Y. Ichinose, K. Nozaki, K. Fugami, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 62, 143 (1989).
30. T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 21, 71 (1980); R. Noyori, S. Murata, and M. Suzuki, Tetrahedron, 37, 3899 (1981).
31. T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 21, 71 (1980); R. Noyori, S. Murata, and M. Suzuki, Tetrahedron, 37, 3899 (1981).
32. T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 21, 4679 (1979).
33. 2: C, 74.19; H, 9.34%.
34. The β-siloxyester was prepared by t-butyldimethylsilylation of syn β-hydroxyester generated according to the reported procedure. M. Taniguchi, H. Fujii, K. Oshima, and K. Utimoto, Tetrahedron, 49, 11169 (1993).
35. C. Chatgilialoglu, Acc. Chem. Res., 25, 188 (1992); B. Giese and B. Kopping, Tetrahedron Lett., 30, 681 (1989).
36. C. Chatgilialoglu, Acc. Chem. Res., 25, 188 (1992); B. Giese and B. Kopping, Tetrahedron Lett., 30, 681 (1989).
37. Y. Ueno, K. Chino, M. Watanabe, O. Moriya, and M. Okawara, J. Am. Chem. Soc., 104, 5564 (1982); G. Stork, R. Mook, Jr., S. A. Biller, and S. D. Rychnovsky, J. Am. Chem. Soc., 105, 3741 (1983).
38. Y. Ueno, K. Chino, M. Watanabe, O. Moriya, and M. Okawara, J. Am. Chem. Soc., 104, 5564 (1982); G. Stork, R. Mook, Jr., S. A. Biller, and S. D. Rychnovsky, J. Am. Chem. Soc., 105, 3741 (1983).