Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues

European Journal of Organic Chemistry

Volumn , Issue 33, 2009, Pages 5788-5795

  Coulombel, Lydie ^a   Weïwer, Michel ^a   Duñach, Elisabet ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

Alcohols; Alkenes; Aluminum; Cyclization; Superacids systems

Indexed keywords

EID: 72849144248     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900841     Document Type: Article

References (40)

1. a) G. Cardillo, M. Orena, Tetrahedron 1990, 46, 3321-3408;
2. b) P. A. Bartlett, Tetrahedron 1980, 36, 2-72;
3. c) T. L. B. Boivin, Tetrahedron 1987, 43, 3309-3362;
4. d) H. Kotsuki, Synlett 1992, 97-106;
5. e) M. C. Elliot, J. Chem. Soc. Perkin Trans. 1 2000, 1291-1318;
6. f) M. C. Elliot, E. Williams, J. Chem. Soc. Perkin Trans. 1 2001, 2303-2340.
7. K. Tani, Y. Katoaka in Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grutzmacher), Wiley-VCH, Weinheim, 2001.
8. L. Coulombel, E. Duñach, Green Chem. 2004, 6, 499-501.
9. L. Coulombel, I. Favier, E. Duñach, Chem. Commun. 2005, 17, 2286-2288.
10. L. Coulombel, M. Rajzmann, J. M. Pons, S. Olivero, E. Duñach, Chem. Eur. J. 2006, 12, 6356-6365.
11. H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc, 2004, 126, 9536-9537.
12. K. Komeyama, T. Morimoto, Y. Nakayama, K. Takaki, Tetrahedron Lett. 2007, 48, 3259-3261.
13. I. Kamiya, H. Tsunoyama, T. Tsukuda, H. Sakurai, Chem. Lett. 2007, 36, 646-647.
14. D. D. DesMarteau, Science 2000, 289, 72-73.
15. L. Coulombel, F. Grau, M. Weiwer, I. Favier, X. Chaminade, A. Heumann, J. C. Bayón, P. Aguirre, E. Duñach, Chem. Biodiversity 2008, 5, 1070-1082.
16. a) F. Seidel, M. Stoll, Helv. Chim. Acta 1959, 42, 1830-1844;
17. b) C. F. Seidel, D. Felix, A. Eschenmoser, K. Biemann, E. Palluy, M. Stall, Helv. Chim. Acta 1961, 44, 598-606.
18. a) P. Werkhoff, M. Guentert, G. Krammer, H. Sommer, J. Kaulen, J. Agric. Food Chem. 1998, 46, 1076-1096;
19. b) L. Mondello, A. Verzera, I. Bonaccorsi, J. U. Chowdhury, Y. J. Begum, J. Essent. Oil Res. 1998, 10, 185-188;
20. c) N. Jain, K. K. Aggarwal, K. V. Syamasundar, S. K. Srivastava, S. Kumar, Flavour Fragr. J. 2001, 16, 44-46.
21. a) R. L. Snowden, S. M. Linder, B. L. Muller, K. H. ShulteElte, Helv. Chim. Acta 1987, 70, 1879-1885;
22. b) E. H. Eschinasi, J. Org. Chem. 1970, 35, 1097-1100;
23. c) T. Yamamoto, H. Matsuda, Y. Utsumi, T. Hagiwara, T. Kanisawa, Tetrahedron Lett. 2002, 43, 9077-9080;
24. d) M. Demuth, X. Xing, K. Schaffner, Patent DE 19942997, 2001;
25. e) S. C. Taneja, V. K. Sethi, S. Koul, S. S. Andotra, G. N. Qazi, US Patent 2003186395, 2003.
26. H. Watkins, O. C. Liu, J. A. Krivda, Patent US 5219836, 1993.
27. P. Kraft, J. A. Bajgrowicz, C. Denis, G. Frater, Angew. Chem. Int. Ed. 2000, 39, 2980-3010.
28. D. Yang, C. Zhang, J. Org. Chem. 2001, 66, 4814-4818.
29. Y. L. Zhong, T. K. M. Shing, J. Org. Chem. 1997, 62, 2622-2624.
30. 3 by using the MM2 method.
31. Olfactory evaluations were realised in 1% ethanolic solution by V. Mane & Fils S. A. (Bar sur Loup, France) and Rhodia Organique (Lyon, France).
32. E. Brenna, C. Fuganti, S. Ronzani, S. Serra, Can. J. Chem. 2002, 80, 714-723.
33. a) M. K. Agrawal, S. Adimurthy, B. Ganguly, P. K. Ghosh, Tetrahedron 2009, 65, 2791-2797;
34. b) S. C. Tanaja, V. K. Sethi, S. S. Andotra, S. Koul, G. N. Qazi, Synth. Commun. 2005, 35, 2297-2303;
35. c) B. Gawdzik, R. Obara, J. Zon, C. Wawrzenczyk, Phosphorus, Sulfur Silicon Relat. Elem. 1996, 117, 139-147.
36. a) X.-F. Ren, E. Turos, C. H. Lake, M. R. Churchill, J. Org. Chem. 1995, 60, 6468-6483;
37. b) D. J. Hart, S. Patterson, A. Zakarian, Heterocycles 2000, 52, 1025-1028.
38. P. G. Andersson, J.-E. Bäckvall, J. Org. Chem. 1991, 56, 5349-5353.
39. a) C. Fuganti, P. Grasselli, J. Chem. Soc., Chem. Commun. 1979, 995-997;
40. b) O. Kitagawa, M. Yoshikawa, H. Tanabe, T. Morita, M. Takahashi, Y. M. Dobashi, T. Taguchi, J. Am. Chem. Soc. 2006, 128, 12923-12931.