Triflic acid-catalysed cyclisation of unsaturated alcohols

Green Chemistry

Volumn 6, Issue 10, 2004, Pages 499-501

  Coulombel, Lydie ^a   Duñach, Elisabet ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 9144230111     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408760g     Document Type: Article

References (36)

1. (a) T. L. B. Boivin, Tetrahedron, 1987, 43, 3309;
2. (b) G. Cradillo and M. Orena, Tetrahedron, 1990, 46, 3321-3408;
3. (c) H. Kotsubi, Synlett, 1992, 97;
4. (d) P. A. Bartlett, Tetrahedron, 1980, 36, 2.
5. (a) A. F. Morris, E. Naef, S. Escher and A. Velluz, U.S. Patent 5068362, 1991;
6. (b) A. R. Hochstetler, U.S. Patent 4549029, 1985;
7. (c) P. D. Noire, U.S. Patent 5510326, 1996;
8. (d) J. F. Vinals, R. Bank, J. Kiwala, D. E. Hrusa, J. B. Hall and M. H. Vock, U.S. Patent 4115406, 1978;
9. (e) A. J. A. van der Weerdt, R. Plomp and W. Apeldoorn, U.S. Patent 4404127, 1983.
10. A. P. S. Narula, Perfum. Flavor., 2003, 28, 62.
11. (a) S. P. Chavan and A. K. Sharma, Tetrahedron Lett., 2001, 42, 4923;
12. (b) S. P. Bew, J. M. Barks, D. W. Knight and R. J. Middleton, Tetrahedron Lett., 2000, 41, 4447;
13. (c) S. B. Bedford, K. E. Bell, F. Bennett, C. J. Hayes, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1999, 2143;
14. (d) S. H. Kang and S. B. Lee, Tetrahedron, 1993, 34, 1955;
15. (e) S. D. Rychnovsky and P. A. Bartlett, J. Am. Chem. Soc., 1981, 103, 3963.
16. (a) M. Gruttadauria, C. Aprile, S. Riela and R. Noto, Tetrahedron Lett., 2001, 42, 2213;
17. (b) B. Lipshutz and T. Gross, J. Org. Chem., 1995, 60, 3572;
18. (c) K. C. Nicolaou, R. L. Magolda, W. J. Sipio, W. E. Barnette, Z. Lysenko and M. M. Joullie, J. Am. Chem. Soc., 1980, 102, 3784.
19. (a) S. O. Kang, J. H. Lee and S. B. Lee, Tetrahedron Lett., 1998, 39, 59;
20. (b) A. Garavelas, I. Mavropoulos, P. Perlmutter and G. Westman, Tetrahedron Lett., 1995, 36, 463;
21. (c) P. Audin, A. Doutheau and J. Gore, Bull. Soc. Chim. Fr., 1984, 7-8, 297.
22. (a) M. A. Arai, M. Kuraishi, T. Arai and H. Sasai, J. Am. Chem. Soc., 2001, 123, 2907;
23. (b) I. Macsari and K. Szabo, Tetrahedron Lett., 2000, 1119;
24. (c) G. V. M. Sharma, A. S. Chander, K. Krishnudu and P. R. Krishna, Tetrahedron Lett., 1998, 6957.
25. (a) M. L. J. Mihailovic and D. Marinkovic, J. Serb. Chem. Soc., 1985, 50, 5;
26. (b) M. L. J. Mihailovic, N. Orbovic and D. Marinkovic, Bull. Soc. Chim. Beograd, 1979, 44, 597;
27. (c) R. Paul and H. Normant, Bull. Soc. Chim. Fr., 1944, 11, 365;
28. (d) J. Colonge and A. Lagier, Bull. Soc. Chim. Fr., 1949, 1, 15;
29. (e) O. Riobé, Ann. Chim. (Paris), 1949, 12, 632;
30. (f) C. Crisan, Ann. Chim. (Paris), 1956, 13, 467.
31. X. Franck, B. Figadère and A. Cavé, Tetrahedron Lett., 1997, 38, 1413.
32. (a) K. Miura, S. Okajima, T. Hondo, T. Nakagawa, T. Takahashi and A. Hosomi, J. Am. Chem. Soc., 2000, 122, 11348;
33. (b) K. Miura, T. Hondo, T. Takahashi and A. Hosomi, Tetrahedron Lett., 2000, 2129.
34. 13C-NMR and mass spectrometry.
35. 1H-NMR data (200 MHz): 2a: 3.7 (1 H, dqd, J = 12.3, 6.2, 2.0 Hz), 1.7-1.3 (6 H, m), 1.21 (3 H, s), 1.19 (3 H, s), 1.1 (3 H, d, J = 6.2 Hz); 2b: 3.8 (2 H, t, J = 6.8 Hz), 1.9 (2 H, m), 1.7 (2 H, t, J = 7.7 Hz), 1.2 (6 H, s); 2c: 7.2-7.0 (2 H, m), 6.8-6.6 (2 H, m), 4.8 (1 H, ddq, J = 8.8, 7.7, 6.3 Hz), 3.2 (1 H, dd, J = 15.4, 8.8 Hz), 2.7 (1 H, dd, J = 15.4, 7.7 Hz), 1.4 (3 H, d, J = 6.3 Hz). 2d: 3.8-3.6 (3 H, m), 1.6-1.9 (4 H, m), 1.5 (2 H, m), (3 H, t, J = 7.4 Hz); 2e: 3.9-3.6 (3 H, m), 1.9-1.7 (3 H, m), 1.5-1.1 (11 H, m), 0.8 (3 H, t, J = 6.8 Hz); 2e′: 3.9-3.6 (3 H, m), 1.6-1.1 (14 H, m), 0.8 (3 H, t, J = 6.8 Hz). 2f: 7.4-7.2 (5 H, m), 4.3 (1 H, m), 4.1 (1 H, m), 3.6 (1 H, m), 2.0-1.5 (6 H, m). 2g: 4.0-3.8 (3 H, m), 3.7 (1 H, ddd, J = 8.1, 7.7, 6.4 Hz), 2.1-1.8 (3 H, m), 1.5-1.3(1 H, m), 1.2 (3 H, d, J = 6.1 Hz).
36. R. Effenberger, J. Chem. Technol. Biotechnol., 1993, 58, 129.