Regioselectivity of ring closure of 2-thia- and 2-sulfonyl-5-methyl-5-hexenyl radicals

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4065-4067

  Della, Ernest W ^a   Graney, Sean D ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0042738090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0267836     Document Type: Article

References (32)

1. (a) For an extensive review on "Radicals in natural product synthesis" see: Curran, D. P.; Fevig, T. L.; Jasperse, C. P. Chem. Rev. 1991, 91, 1237.
2. (b) Curran, D. P. Synlett 1991, 63.
3. (c) Neumann, W. P. Synthesis 1987, 665.
4. (d) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J., Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
5. (a) Della, E. W.; Smith, P. A. J. Chem. Soc., Perkin Trans. 1 2001, 445.
6. (b) Della, E. W.; Smith, P. A. Tetrahedron Lett. 2001, 42, 481.
7. (c) Della, E. W.; Smith, P. A. J. Org. Chem. 2000, 65, 6627.
8. (d) Della, E. W.; Smith, P. A. J. Org. Chem. 1999, 64, 1798.
9. (e) Della, E. W.; Smith P. A.; Knill, A. M. Chem. Commun. 1996, 14, 1637.
10. (f) Della, E. W.; Knill, A. M. Tetrahedron Lett. 1996 37, 5805.
11. (g) Della, E. W.; Knill, A. M. J. Org. Chem. 1996, 61, 7529.
12. (h) Della, E. W.; Knill, A. M. Aust. J. Chem. 1995, 48, 2047.
13. Serra, A. C.; da Silva Correa, C. M. M. Tetrahedron Lett. 1991, 32, 6653.
14. Ponaras, A. A.; Zaim, O. Tetrahedron Lett. 2000, 41, 2279.
15. Vacher, B.; Samat, A.; Allouche, A.; Laknifli, A.; Baldy, A.; Chanon, M. Tetrahedron 1988, 44, 2925.
16. Ke, B.-W.; Lin, C.-H.; Tsai, Y.-M. Tetrahedron 1997, 53, 7805.
17. Della, E. W.; Graney, S. D. Tetrahedron Lett. 2000, 41, 7987.
18. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
19. 2), and 9 are provided in Suppporting Information.
20. Crich, D.; Yao, Q. J. Org. Chem. 1995, 60, 84.
21. Maxwell, B. J.; Smith, B. J.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 2000, 425.
22. 3SnH.
23. 14b spectral data were identical to those reported.
24. (a) Kropp, P. J.; Breton, G. W.; Fields, J. D.; Tung, J. C.; Loomis, B. R. J. Am. Chem. Soc. 2000, 122, 4280.
25. (b) Barbarella, G.; Dembech, P. Org. Magn. Res. 1984, 22, 402.
26. Beckwith, A. L. J.; Lawrence, T. J. Chem. Soc., Perkin Trans. 2 1979, 1535.
27. Beckwith, A.; L. J.; Blair, I. A.; Phillipou, G. Tetrahedron Lett. 1974, 2251.
28. 2). albeit in very low yield. (a) Wilt, J. J. Org. Chem. 1981, 103, 5251; Tetrahedron 1985, 41, 3979.
29. 2). albeit in very low yield. (a) Wilt, J. J. Org. Chem. 1981, 103, 5251; Tetrahedron 1985, 41, 3979.
30. (b) Wilt, J. W.; Lustztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281.
31. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976.
32. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701.