[3.3] Sigmatropy within 1-Vinyl-2-alkenyl-7,7-dimethyl-exo-norbornan-2-ols. The First Atropselective Oxyanionic Cope Rearrangement

Journal of the American Chemical Society

Volumn 112, Issue 1, 1990, Pages 277-283

  Paquette, Leo A ^a   Pegg, Neil A ^a   Toops, Dana ^a   George, D ^a   Rogers, Robin D ^b  

^a OHIO STATE UNIVERSITY   (United States)

^b Northern Illinois University ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0025342942     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00157a043     Document Type: Article

References (37)

1. Hill, R. K. In Asymmetric Synthesis: Morrison, J. D., Ed.; Academic Press, 1984; Vol. 3A, p 503.
2. Hill, R. K. In Comprehensive Organic Synthesis: Pergamon Press; in press.
3. Paquette, L. A.; He, W.; Rogers, R. D. J. Org. Chem. 1989, 54, in press.
4. Paquette, L. A. In Organic Synthesis: Modern Trends; Chizhov, O., Ed.; Blackwell Scientific Publications: 1988; pp 1-12.
5. Paquette, L. A.; Learn, K. S. J. Am. Chem. Soc. 1986, 108, 7873.
6. Paquette, L. A.; Romine, J.L.; Lin, H.-S. Tetrahedron Lett. 1987, 28, 31.
7. Paquette, L. A.; Learn, K. S.; Romine, J. L. Tetrahedron 1987, 43, 4989.
8. Paquette, L. A.; Learn, K. S.; Romine, J. L.; Lin, H.-S. J. Am. Chem. Soc. 1988, 110, 879.
9. Paquette, L. A.; DeRussy, D. T.; Cottrell, C. E. J. Am. Chem. Soc. 1988, 110, 890.
10. Paquette, L. A.; DeRussy, D. T.; Gallucci, J. C. J. Org. Chem. 1989, 54, in press.
11. Paquette, L. A.; DeRussy, D. T.; Pegg, N. A.; Taylor, R. T.; Zydowsky, T. M. J. Org. Chem. 1989, 54, 4576.
12. Doering, W. von E.; Roth, W. R. Tetrahedron 1962, 18, 67.
13. Gajewski, J. J.; Jimenez, J. L. J. Am. Chem. Soc. 1986, 108, 468.
14. Gajewski, J. J.; Benner, C. W.; Hawkins, C. M. J. Org. Chem. 1987, 52, 5198.
15. Paquette, L. A.; Teleha, C. A.; Taylor, R. T.; Maynard, G. D.; Rogers, R. D.; Gallucci, J. C.; Springer, J. P., preceding paper in this issue.
16. Fischer, N.; Opitz, G. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, p 877.
17. Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233.
18. Imamoto, T.; Sugiura, Y. J. Organomet. Chem. 1985, 285, C21.
19. Imamoto, T.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763.
20. Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 1835.
21. Macdonald, T. L.; Natalie, K. J., Jr.; Prasad, G.; Sawyer, J. S. J. Org. Chem. 1986, 51, 1124.
22. VanderWerf, C. A.; Heisler, R. Y.; McEwen, W. E. J. Am. Chem. Soc. 1954, 76, 1231.
23. Vince, R.; Deluge, S. J. Med. Chem. 1974, 17, 578.
24. Trost, B.; Fray, M. J. Tetrahedron Lett. 1988, 29, 2163.
25. Naqvi, S. M.; Horwitz, J. P.; Filler, R. J. Am. Chem. Soc. 1957, 79, 6283.
26. Shill, C.; Swenton, J. S. J. Org. Chem. 1982, 47, 2825.
27. Oki, M. Top. Stereochem. 1983, 14, 1.
28. Oki, M. Acc. Chem. Res. 1984, 17, 154.
29. Shea, K. J.; Gilman, J. W. Tetrahedron Lett. 1983,657.
30. Shea, K. J.; Gilman, J. W.; Haffner, C. D.; Dougherty, T. K. J. Am. Chem. Soc. 1986, 108, 4953.
31. Koreeda, M.; Tanaka, Y.; Schwartz, A. J. Org. Chem. 1980, 45, 1172.
32. Clive, D. L. J.; Russell, G.C.; Suri, S. C. J. Org. Chem. 1982, 47, 1632.
33. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774.
34. Shirahama, H.; Hayano, K.; Kanemoto, Y.; Misumi, S.; Ohtsuka, T.; Hashiba, N.; Furusaki, N.; Murata, S.; Noyori, R.; Matsumoto, T. Tetrahedron Lett. 1980, 21, 4835.
35. Sheldrick, G. M. SHBLX76, a system of computer programs for X-ray structure determination as locally modified, University of Cambridge, England, 1976.
36. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV, pp 72, 99, 149.
37. Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; Declercq, J.-P.; Woolfson, M. M. MULTAN 80, A system of computer programs for the automatic solution of crystal structures from X-ray diffraction data, Universities of York, England, and Louvain, Belguim.