Lewis acid mediated intermolecular vinylsilylation of alkynes

Chemistry Letters

Volumn , Issue 10, 2001, Pages 982-983

  Asao, Naoki ^a   Nabatame, Kazuyuki ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035541333     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.982     Document Type: Article

References (24)

1. For reviews, see: a) "Lewis Acids in Organic Synthesis," ed. by H. Yamamoto, Wiley-VCH, Weinheim (2000), Vol. 1-2.
2. b) I. Marek and J. F. Normant, in "Metal-catalyzed Cross-coupling Reactions," ed. by F. Diederich and P. J. Stang, Wiley-VCH, Weinheim (1998), p 271.
3. P. Knochel, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 4, p 865.
4. N. Asao and Y. Yamamoto, Bull. Chem. Soc. Jpn., 73, 1071 (2000).
5. For Al, see: a) G. Wilke and H. Muller, Chem Ber., 89, 444 (1956).
6. b) G. Wilke and H. Muller, Justus Liebigs Ann. Chem., 618, 267 (1958).
7. J. J. Eisch and W. C. Kaska, J. Am. Chem. Soc., 88, 2213 (1966).
8. G. Zweifel, J. T. Snow, and C. C. Whitney, J. Am. Chem. Soc., 90, 7139 (1968).
9. For Cu, see: a) J. F. Normant and A. Alexakis, Synthesis, 1981, 841.
10. b) A. Alexakis and J. F. Normant, Tetrahedron Lett., 23, 5151 (1982).
11. M. Furber, R. J. K. Taylor, and S. C. Burford, Tetrahedron Lett., 26, 3285 (1985).
12. M. Furber, R. J. K. Taylor, and S. C. Burford, J. Chem. Soc., Perkin Trans. 1, 1986, 1809.
13. For Mg, see: H. G. Richey, Jr. and F. W. Von Rein, J. Organomet. Chem., 20, 32 (1969).
14. For Zr, see: T. Takahashi, D. Y. Kondakov, Z. Xi, and N. Suzuki, J. Am. Chem. Soc., 117, 5871 (1995).
15. N. Asao, T. Shimada, and Y. Yamamoto, J. Am. Chem. Soc., 121, 3797 (1999).
16. While the reaction of 1e with Z-pentyl-substituted vinylsilane instead of 2 was examined, the desired vinylsilylation product was not obtained and a complex mixture was produced.
17. a) D. A. Evans, B. D. Allison, and M. G. Yang, Tetrahedron Lett., 40, 4457 (1999).
18. b) D. A. Evans, K. T. Chapman, and J. Bisaha, J. Am. Chem. Soc., 110, 1238 (1988).
19. a) N. Asao, T. Asano, T. Ohishi, and Y. Yamamoto, J. Am. Chem. Soc., 122, 4817 (2000).
20. b) N. Asao, T. Shimada, and Y. Yamamoto, Tetrahedron Lett., 41, 9533 (2000).
21. N. Asao, T. Ohishi, K. Sato, and Y. Yamamoto, J. Am. Chem. Soc., 123, 6931 (2001).
22. It is well known that vinylsilanes react with electrophiles with retention of configuration, see: a) E. W. Colvin, "Silicon in Organic Synthesis," Butterworth, London (1981).
23. b) W. P. Weber, "Silicon Reagents for Organic Chemistry," Springer Verlag, Berlin (1983).
24. I. Fleming, J. Dunoguès, and R. Smithers, Org. React. (N.Y.), 37, 57 (1989).