Transition metal-assisted transformations of diversely functionalized dienynes

European Journal of Organic Chemistry

Volumn , Issue 9, 2003, Pages 1759-1764

  Marco Contelles, José ^a   Mainetti, Emily ^b   Fensterbank, Louis ^b   Malacria, Max ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b CNRS   (France)

Author keywords

Carbocycles; Dienynes; Free radical cyclization

Indexed keywords

4 ETHYNYL 2,6,6 TRIMETHYLOCTA 1,7 DIEN 4 OL; 4 ETHYNYL 6,6 DIMETHYLOCTA 1,7 DIEN 4 OL; ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; FREE RADICAL; PALLADIUM; TIN DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; ISOMERISM; STEREOCHEMISTRY;

EID: 0038666254     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200310007     Document Type: Article

References (35)

1. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834.
2. [2a] J. Marco-Contelles, J. Ruiz-Caro, E. Mainetti, P. Devin, L. Fensterbank, M. Malacria, Tetrahedron 2002, 58, 1147-1158.
3. [2b] E. Mainetti, V. Mouriès, L. Fensterbank, M. Malacria, J. Marco-Contelles, Angew. Chem. Int. Ed. 2002, 41, 2132-2135.
4. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
5. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
6. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
7. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
8. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
9. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
10. [3a] A. G. Davies, Organotin Chemistry, Wiley-VCH, Weinheim, 1997. [3b] M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, London, 1987. For some selected papers on this subject, see: [3c] G. Stork, R. Mook, Jr., J. Am. Chem. Soc. 1987, 109, 2829-2831. [3d] D. L. J. Clive, H. W. Manning, J. Chem. Soc., Chem. Commun. 1993, 666-667. [3e] O. Moriya, M. Okawara, Y. Ueno, Chem. Lett. 1984, 1437-1440. [3f] N. Moufid, Y. Chapleur, Tetrahedron Lett. 1991, 32, 1799-1802. [3g] J. Marco-Contelles, C. Destabel, P. Gallego, J. L. Chiara, M. Bernabé, J. Org. Chem. 1996, 61, 1354-1362.
11. [4a] B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, New York, 1986.
12. [4b] D. P. Curran, Synthesis 1988, 417-439, 489-513.
13. [4c] W. B. Motherwell, D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992.
14. [5a] R. A. Bunce, Tetrahedron 1995, 51, 13103-13159.
15. [5b] M. Malacria, Chem. Rev. 1996, 96, 289-306.
16. [5c] A. J. McCarroll, J. C. Walton, Angew. Chem. Int. Ed. 2001, 40, 2224-2248.
17. N. Nozaki, K. Oshima, K. Utimoto, Bull. Soc. Chem. Jpn. 1987, 60, 3465-3467.
18. For a review on organoboranes as a source of radicals, see: C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415-3434.
19. [8a] J. Marco-Contelles, Chem. Commun. 1996, 2629-2630.
20. [8b] J. Marco-Contelles, Synth. Commun. 1997, 27, 3163-3170.
21. G. Stork, R. Mook, Tetrahedron Lett. 1986, 27, 4529-4532.
22. [10a] M. Pereyre, J.-P. Quintard, Pure Appl. Chem. 1981, 53, 2401-2417.
23. [10b] E. J. Corey, R. H. Wollenberg, J. Org. Chem. 1975, 40, 2265-2266.
24. H. E. Ensley, R. R. Buescher, K. Lee, J. Org. Chem. 1982, 47, 404-408.
25. B. Alcaide, J. L. Benito, I. M. Rodríguez-Campos, J. Rodríguez-López, A. Rodríguez-Vicente, M. A. Sierra, S. GarcíaGranda, A. Gutiérrez-Rodríguez, Tetrahedron: Asymmetry 1995, 6, 1055-1058.
26. 31ClOSn. Unit cell parameters: a = 11.181(3), b = 10.238(5), c= 20.835(7), β = 92.99(2). Space group P21/c.
27. [14a] S.-W. Ng, J. J. Zuckerman, J. Organomet. Chem. 1982, 234, 257-275.
28. [14b] H. Gilman, F. K. Cartledege, S.-Y. Sim, J. Organomet. Chem. 1965, 4, 332-334.
29. A. L. J. Beckwith, C. H. Schiesser, Tetrahedron 1985, 41, 3925-3941.
30. T. V. RajanBabu, Acc. Chem. Res. 1991, 24, 139-145.
31. [17a] M. Lautens, J. Mancuso, Synlett 2002, 394-398.
32. [17b] S.K. Kang, Y.-H. Ha, B.-S. Ko, Y. Lim, J. Jung, Angew. Chem. Int. Ed. 2002, 41, 343-345.
33. [17c] T. V. RajanBabu, S. Shun, J. Am. Chem. Soc. 2001, 123, 8416-8417.
34. [17d] M. Mori, T. Hirose, H. Wakamatsu, N. Imakuni, Y. Sato, Organometallics 2001, 20, 1907-1909.
35. We have analyzed the cycloisomerization reaction of compound 1 - with or without allyltrimethylsilane - in the presence of Grubbs' catalyst, but without success (a complex reaction mixture was observed, and we recovered most of the starting material unaltered).