Functionalized Bicyclo[3.3.0]octanes by Enantioselective Transannular Desymmetrization

Organic Letters

Volumn 3, Issue 3, 2001, Pages 441-444

  Hodgson, David M ^a   Cameron, Iain D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000551427     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006947n     Document Type: Article

References (33)

1. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784.
2. (a) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
3. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
4. (a) Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361-14384.
5. (b) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457.
6. (a) Cope, A. C.; Lee, H.-H.; Petree, H. E. J. Am. Chem. Soc. 1958, 80, 2849-2852.
7. (b) Whitesell, J. K.; White, P. D. Synthesis 1975, 602-603.
8. (c) Boeckman, R. K., Jr. Tetrahedron Lett. 1977, 4281-4284.
9. Reviews: (d) Cope, A. C.; Martin, M. M.; McKervey, M. A. Q. Rev., Chem. Soc. 1966, 20, 119-152.
10. (e) Crandall, J. K.; Apparu, M. Org. React. (N.Y.) 1983, 29, 345-443.
11. (f) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
12. (a) Hodgson, D. M.; Lee, G. P. Chem. Commun. 1996, 1015-1016.
13. (b) Hodgson, D. M.; Lee, G. P. Tetrahedron: Asymmetry 1997, 8, 2303-2306.
14. (c) Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witherington, J. J. Chem. Soc., Perkin Trans. 1 1998, 2151-2161.
15. (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 2283-2316.
16. (b) Beak, P.; Bass, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
17. Hodgson, D. M.; Robinson, L. A. Chem. Comm. 1999, 309-310.
18. (a) Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-720.
19. (b) Pirrung, M. C.; Morehead, A. T., Jr.; Young, B. G. In The Total Synthesis of Natural Products; Goldsmith, D., Ed.; Wiley: New York, 2000; Vol. 11, pp 117-186, 275-357.
20. (a) Alvarez, E.; Diaz, M. T.; Perez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martin, J. D. J. Org. Chem. 1994, 59, 2848-2876.
21. (b) VanRheenen, V.; Cha, D. Y.; Hartley, W. M. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 342-348.
22. Powell, K. A.; Hughes, A. L.; Katchian, H.; Jerauld, J. F.; Sable, H. Z. Tetrahedron 1972, 28, 2019-2027.
23. Dolan, S. C.; MacMillan, J. J. Chem. Soc., Chem. Commun. 1985, 1588-1589.
24. Lemke, K.; Ballschuh, S.; Kunath, A.; Theil, F. Tetrahedron: Asymmetry 1997, 8, 2051-2055.
25. Whitesell, J. K.; Matthews, R. S. J. Org. Chem. 1977, 42, 3878-3882.
26. Hodgson, D. M.; Maxwell, C. R.; Matthews, I. R. Tetrahedron: Asymmetry 1999, 10, 1847-1850.
27. Singh, V. K.; Saravanan, P.; DattaGupta, A.; Bhuniya, D. Tetrahedron 1997, 53, 1855-1860; 1998, 54, 13323 (Errata).
28. Cope, A. C.; Fisher, B. S.; Funke, W.; McIntosh, J. M.; McKervey, M. A. J. Org. Chem. 1969, 34, 2231-2234.
29. For other observations of changes in product profile when using an organolithium with sparteine compared with TMEDA, see: (a) Park, Y. S.; Beak, P. J. Org. Chem. 1997, 64, 22996-2997. (b) Park, V. S.; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 10537-10538.
30. For other observations of changes in product profile when using an organolithium with sparteine compared with TMEDA, see: (a) Park, Y. S.; Beak, P. J. Org. Chem. 1997, 64, 22996-2997. (b) Park, V. S.; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 10537-10538.
31. Kraus, M. Collect. Czech. Chem. Commun. 1972, 37, 460-465.
32. (a) Morgan, K. M.; Gronert, S. J. Org. Chem. 2000, 65, 1461-1466.
33. (b) Ramirez, A.; Collum, D. B. J. Am. Chem. Soc. 1999, 121, 11114-11121.