Stereoselectivity in free radical cyclization of 1,6 and 1,7 enynes with Tris(trimethylsilyl)silane

Boletin de la Sociedad Chilena de Quimica

Volumn 43, Issue 3, 1998, Pages 259-266

  Martin, Jaime ^a   Jaramillo, Luz Marina ^a  

^a UNIVERSIDAD DEL VALLE   (Colombia)

Author keywords

Enynes silylation, Tris(trimethylsilyl) silane; Stercoselective radical cyclization; Tris(trimethylsilul) silyl vinyl radicals

Indexed keywords

EID: 0004223665     PISSN: 03661644     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. (a) D.P. Curran, N.A. Porter, B. Giesse. Stereochemistry of Radical Reactions Concepts, Guidelines, and Synthetic Applications VCH, New York (1996).
2. (b) W.B. Motherwell, D. Crich. Free Rdical Chain Reactions in Organic Synthesis; Academic Press, New York 81992).
3. (c) D.P. Curran. Radical Cyclizations and Sequential Radical Reactions in Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency. Eds. Trost, B.M. and Fleming, I. Pergamon Press, V. 4, 779-831 (1991).
4. (d) D.P. Curran. Synthesis 417-439 (1988).
5. (e) M. Ramaiah. Tetrahedron, 43, 3541-3676 (1987).
6. (a) C. Chatgilialoglu. Chem. Rev., 95, 1229 (1995).
7. (b) C. Chatgilialoglu. Acc. Chem. Res., 25, 188 (1992).
8. C. Chatgilialoglu, B. Giese and B. Kopping. Tetrahedron, 40, 3963 (1990).
9. C. Chatgilialoglu, B. Kopping, B. Giese and M. Zehender. J. Org. Chem., 57, 3994 (1992).
10. (a) M. Ihara, F. Setsu, M. Shohda, N. Taniguchi, Y. Tokunaga, K. Fukumoto. J. Org. Chem., 59, 5317 (1994).
11. (b) S. Kim, G.H. Joe, J.Y. Do. J. Am. Chem. Soc., 116, 5521 (1994).
12. (c) J.E. Lyons, C.H. Schieser, K.J. Sutej. J. Org. Chem., 58, 5632 (1993).
13. (d) C. Chatgilialogl, B. Giese and B. Kopping. Tetrahedron Lett., 40, 6013 (1990).
14. (e) B. Giese and B. Kopping. Tetrahedron Lett. Ibid, 30, 681 (1989).
15. (a) J. Cossi and L. Sallè. Tetrahedron Lett., 36, 7235 (1995).
16. (b) K. Miura, K. Oshima, K. Utimoto. Bull. Chem. Soc. Jpn., 66, 2348 (1993).
17. (c) G. Pattenden, D.J. Schultz. Tetrahedron Lett., 34, 6787 (1993).
18. (d) K.J. Kulicke, C. Chatgilialoglu, B. Kopping and B. Giese. Helv. Chim. Acta, 75, 935 (1992).
19. (e) G.A. Kraus and S. Liras. Tetrahedron Lett., 31, 5265 (1990).
20. (f) B. Giese and K.J. Kulicke. Synlett., 90 (1990).
21. W. Still, M. Kahn and A. Mitra. J. Org. Chem., 43, 2923 (1978).
22. G. Stork and R. Mook Jr. J. Am. Chem. Soc., 109, 2829 (1987).
23. T. Kataoka, M. Yoshimatsu, Y. Noda, T. Sato, H. Shimizo and M. Hori. J. Chem. Soc. Perkin Trans, 1, 121 (1993).
24. L.M. Jaramillo, J. Martin and R. Moreno. Acta Cryst. (submitted).
25. (a) E.L. Cochran, F.J. Adrian, V.A. Bowers. J. Chem. Phys., 40, 213 (1964).
26. (b) R.W. Fessenden, R.H. Schuler. J. Chem. Phys. Ibid, 39, 2147 (1963).
27. (a) A.L.J. Beckwith, C.H. Schieser. Tetrahedron, 41, 3925 (1985).
28. (b) A.L.J. Schieser. Tetrahedron, Ibid, 37, 3073 (1981).