Highly selective Lewis acid catalyzed Diels-Alder reactions of acyclic (Z)-1,3-dienes

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7402-7403

  Roush, William R ^a   Barda, David A ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOHEXENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030748517     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971070h     Document Type: Article

References (35)

1. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; John Wiley & Sons: New York, 1990.
2. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; pp 315-399.
3. Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753.
4. Roberge, G.; Brassard, P. J. Org. Chem. 1981, 46, 4161.
5. Danishefsky, S. Acc. Chem. Res. 1981, 14, 400.
6. House H. O.; Cronin, T. H. J. Org. Chem. 1965, 30, 1061.
7. Borch, R. F.; Evans, A. J.; Wade, J. J. J. Am. Chem. Soc. 1975, 97, 6282.
8. Oppolzer, W.; Fehr, C.; Warneke, J. Helv. Chim. Acta 1977, 60, 48.
9. Boeckman, R. K., Jr.; Alessi, T. R. J. Am. Chem. Soc. 1982, 104, 3216.
10. Pyne, S. G.; Hensel, M. J.; Fuchs, P. L. J. Am. Chem. Soc. 1982, 104, 5719.
11. Yoshioka, M.; Hakai, H.; Ohno, M. J. Am. Chem. Soc. 1984, 106, 1133.
12. Corey, E. J.; Jardine, P. D. S.; Rohloff, J. C. J. Am. Chem. Soc. 1988, 110, 3672.
13. Deslongchamps, P. Aldrichimica Acta 1991, 24, 43.
14. Jackson, R. W.; Shea, K. J. Tetrahedron Lett. 1994, 35, 1317.
15. Alaimo, C. A.; Coburn, C. A.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 6603.
16. Rubenstein, S. M.; Williams, R. M. J. Org. Chem. 1995, 60, 7215.
17. Winkler, J. D.; Kim, H. S.; Kim, S. Tetrahedron Lett. 1995, 36, 687.
18. Jenkins, P. R. Pure Appl. Chem. 1996, 68, 771.
19. Nicolaou, D. C.; Hwang, C.-K.; Sorensen, E. J.; Clairborne, C. F. J. Chem. Soc., Chem. Commun. 1992, 1117.
20. Okada, K.; Kondo, M.; Tanino, H.; Kakoi, H.; Inoue, S. Heterocycles 1992, 34, 589.
21. Stokes, H. L.; Richardson, B. M.; Wright, M. W.; Vaughn, S. M.; Welker, M. E. Organometallics 1995, 14, 5520.
22. Brocksom, T. J.; Constantino, M. G. J. Org. Chem. 1982, 47, 3450.
23. Gassman, P. G.; Singleton, D. A. J. Am. Chem. Soc. 1984, 106, 7993.
24. Gassman, P. G.; Singleton, D. A. Tetrahedron Lett. 1987, 28, 5969.
25. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182.
26. Bonnert, R. V.; Jenkins, P. R. Tetrahedron Lett. 1987, 28, 697.
27. Engler, T. A.; Sampath, U.; Velde, D. V.; Takusagawa, F. Tetrahedron 1992, 48, 9399.
28. Funk, R. L.; Yost, J. K., III J. Org. Chem. 1996, 61, 2598.
29. Murahashi, S.-I.; Naota, T.; Miyaguchi, N.; Noda, S. J. Am. Chem. Soc. 1996, 118, 2509.
30. Syntheses of dienes 1-3 and details of the stereochemical assignments for cycloadducts 6-8 are provided in the Supporting Information.
31. Stewart, C. A., Jr. J. Org. Chem. 1963, 28, 3320.
32. Rücker, C.; Lang, D.; Sauer, J.; Friege, H.; Sustmann, R. Chem. Ber. 1980, 113, 1663.
33. Mikhael, M. G.; Padias, A. B.; Hall, H. K., Jr. Macromolecules 1993, 26, 5835.
34. Schoepfer, J.; Marquis, C.; Pasquier, C.; Neier, R. J. Chem. Soc., Chem. Commun. 1994, 1001.
35. Heaney, H. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2; p 733.