Base promoted preparation of alkenylsilanols from allylsilanes

Chemistry Letters

Volumn , Issue 10, 1997, Pages 1077-1078

  Akiyama, Takahiko ^a   Imazeki, Shigeaki ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001462649     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1077     Document Type: Article

References (18)

1. G. Stork, T. Y. Chan, and G. A. Breaault, J. Am. Chem. Soc., 114, 7578 (1992).
2. P. Righi, E. Marotta, A. Landuzzi, and G. Rosini, J. Am. Chem. Soc., 118, 9446 (1996). M. Bols and T. Skrydstrup, Chem. Rev., 95, 1253 (1995). M. Maier, in "Organic Synthesis Highlights II," ed by W. Waldmann, VCH, Weinheim (1995), p. 135.
3. P. Righi, E. Marotta, A. Landuzzi, and G. Rosini, J. Am. Chem. Soc., 118, 9446 (1996). M. Bols and T. Skrydstrup, Chem. Rev., 95, 1253 (1995). M. Maier, in "Organic Synthesis Highlights II," ed by W. Waldmann, VCH, Weinheim (1995), p. 135.
4. P. Righi, E. Marotta, A. Landuzzi, and G. Rosini, J. Am. Chem. Soc., 118, 9446 (1996). M. Bols and T. Skrydstrup, Chem. Rev., 95, 1253 (1995). M. Maier, in "Organic Synthesis Highlights II," ed by W. Waldmann, VCH, Weinheim (1995), p. 135.
5. T. H. Chan, L. M. Chen, and D. Wang, J. Chem. Soc., Chem. Commun., 1988, 1280. K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436. L. H. Li, D. Wang, and T. H. Chan, Tetrahedron Lett., 38, 101 (1997).
6. T. H. Chan, L. M. Chen, and D. Wang, J. Chem. Soc., Chem. Commun., 1988, 1280. K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436. L. H. Li, D. Wang, and T. H. Chan, Tetrahedron Lett., 38, 101 (1997).
7. T. H. Chan, L. M. Chen, and D. Wang, J. Chem. Soc., Chem. Commun., 1988, 1280. K. Yamamoto, Y. Kawanami, and M. Miyazawa, J. Chem. Soc., Chem. Commun., 1993, 436. L. H. Li, D. Wang, and T. H. Chan, Tetrahedron Lett., 38, 101 (1997).
8. K. Hirabayashi, A. Mori, and T. Hiyama, Tetrahedron Lett., 1997, 38, 461.
9. S. M. Sieburth and W. Mu, J. Org. Chem., 58, 7584 (1993). A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. A. Mori, H. Sato, K. Mizuno, T. Hiyama, K. Shintani, and Y. Kawakami, Chem. Lett., 1996, 517. K. Takaku, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 37, 6781 (1996).
10. S. M. Sieburth and W. Mu, J. Org. Chem., 58, 7584 (1993). A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. A. Mori, H. Sato, K. Mizuno, T. Hiyama, K. Shintani, and Y. Kawakami, Chem. Lett., 1996, 517. K. Takaku, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 37, 6781 (1996).
11. S. M. Sieburth and W. Mu, J. Org. Chem., 58, 7584 (1993). A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. A. Mori, H. Sato, K. Mizuno, T. Hiyama, K. Shintani, and Y. Kawakami, Chem. Lett., 1996, 517. K. Takaku, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 37, 6781 (1996).
12. S. M. Sieburth and W. Mu, J. Org. Chem., 58, 7584 (1993). A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. A. Mori, H. Sato, K. Mizuno, T. Hiyama, K. Shintani, and Y. Kawakami, Chem. Lett., 1996, 517. K. Takaku, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 37, 6781 (1996).
13. 1H NMR analysis of the mixture showed that 2 was obtained in 89% yield(E/Z = 97:3).
14. Yield of 2 utilizing other bases are as follows: KH; 67%, NaH; 12%, n-BuLi; 0%. When n-BuLi was employed as a base in DMSO, 3 was obtained in 80% yield.
15. Tetramethylsilane is cleaved by KO-t-Bu in DMSO: C. C. Price and J. R. Sowa, J. Org. Chem., 32, 4126 (1967).
16. P. F. Hudrlik, A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982). M. Murakami, M. Suginome, K. Fujimoto, H. Nakamura, P. G. Andersson, and Y. Ito, J. Am. Chem. Soc., 115, 6487 (1993).
17. P. F. Hudrlik, A. M. Hudrlik, and A. K. Kulkarni, J. Am. Chem. Soc., 104, 6809 (1982). M. Murakami, M. Suginome, K. Fujimoto, H. Nakamura, P. G. Andersson, and Y. Ito, J. Am. Chem. Soc., 115, 6487 (1993).
18. F. J. Blanco, P. Cuadrado, A. M. Monzalez, and F. J. Pulido, Synthesis, 1996, 42.