Synthesis of both antipodal forms of 7,7-dimethylbicyclo[2.2.2]oct-2-en-5-one by enantiomer interconversion

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 142-145

  Paquette, Leo A ^a   Tsui, Hon Chung ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002237362     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951552g     Document Type: Article

References (54)

1. (a) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1984; Vol. 3A, 503 ff.
2. (b) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.1.
3. Wilson, S. R. Org. React. (NY) 1993, 43, 93.
4. (a) Paquette, L. A. Synlett 1990, 67.
5. (b) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609.
6. (a) Oplinger, J. A.; Paquette, L. A. Tetrahedron Lett. 1987, 28, 5441.
7. (b) Paquette, L. A.; Oplinger, J. A. Tetrahedron 1989, 45, 107.
8. Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1980, 102, 2463.
9. Evans, D. A.; Golob, A. M.; Mandel, N. S.; Mandel, G. S. J. Am. Chem. Soc. 1978, 100, 8170.
10. (a) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037.
11. (b) Paquette, L. A.; Macdonald, D.; Andreson, L. G. J. Am Chem. Soc. 1990, 112, 9292.
12. (a) Chang, N.-C.; Day, H.-M.; Lu, W.-F. J. Org. Chem. 1989, 54, 4083.
13. (b) Hsieh S.-L.; Chiu, C.-T.; Chang, N.-C. J. Org. Chem 1989, 54, 3820.
14. Jung, M. E ; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614.
15. (a) Paquette, L. A.; Maleczka, R. E., Jr. J. Org. Chem. 1991, 56, 912.
16. (b) Maleczka, R. E., Jr.; Paquette, L. A. J. Org. Chem. 1991, 56, 6538.
17. (a) Martin, S. F.; White, J. B.; Wagner, R. J. Org. Chem. 1982, 47, 3190.
18. (b) Martin, S. F.; Assercq, J.-M.; Austin, R. E.; Dautauarayana, A. P.; Fishpaugh, J. R.; Gluchowski, C.; Guinn, D. E.; Hartmann, M.; Tanaka, T.; Wagner, R.; White, J. B. Tetrahedron 1995, 51, 3455.
19. (a) Paquette, L. A.; Poupart, M.-A. J. Org. Chem. 1993, 58, 4245.
20. (b) Paquette, L. A.; Lassalle, G. Y.; Lovely, C. J. J. Org. Chem. 1993, 58, 4254.
21. (c) Paquette, L. A.; Deaton, D M.; Endo, Y.; Poupart, M.-A. J. Org. Chem. 1993, 58, 4262.
22. (d) Paquette, L. A.; Hormuth, S.; Lovely, C. J. J. Org Chem. 1995, 60, 4813.
23. (a) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1993, 115, 354.
24. (b) Paquette, L. A.; Thompson, R. C. J. Org. Chem. 1993, 58, 4952.
25. (c) Elmore, S. W.; Paquette, L. A. J. Org. Chem. 1993, 58, 4963.
26. (d) Paquette, L. A.; Huber, S K.; Thompson, R. C. J. Org. Chem. 1993, 58, 6874 and relevant earlier references cited therein.
27. Review: Fujita, E.; Node, M. Progress in the Chemistry of Natural Products; Springer Verlag: New York, 1984; Vol. 46, pp 77-157.
28. Synthesis: Fujita, E.; Shibuya, M.; Nakamura, S.; Okada, Y.; Fujita, T. J. Chem. Soc., Perkin Trans. 1 1974, 165.
29. Takeda, Y.; Futatsuishi, Y.; Ichihara, T.; Matsumoto, T.; Terao, H.; Terada, H.; Otsuka, H. Chem. Pharm. Bull. 1993, 41, 685.
30. Sun, H.-D-; Lin, Z.-W.; Niu, F.-D.; Lin, L.-Z.; Chai, H.; Pezzuto, J. M.; Cordell, G. A. J. Nat. Prod. 1994, 57, 1424
31. (a) Yang, Y.-W.; Xu, X.-I.; Wang, D.-H.; Qian, B.-G.; Zhao, Q.-Z. Huaxue Xuebao 1992, 50, 498.
32. (b) Zhou, W.-S.; Chen, Y.-X. Sci. China, Ser B 1992, 35, 194.
33. Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673.
34. Flaugh, M. E.; Crowell, T. A.; Farlow, D. S. J. Org. Chem. 1980, 45, 5399.
35. Review: Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57.
36. Paquette, L. A.; Maleczka, R. E , Jr.; Qiu, F.-Y. J. Org. Chem. 1991, 56, 2455.
37. Menger, F. M., Lee, C. J. Org. Chem. 1979, 44, 3446.
38. Csuk, R.; Glanzer, B. I. Chem. Rev. 1991, 91, 49.
39. (a) Kitahara, T.; Miyake, M.; Kido, M.; Mori, K. Tetrahedron: Asymmetry 1990, 1, 775.
40. (b) Mori, K ; Nagano, E. Biocatalysis 1990, 3, 25.
41. (c) Watanabe, H.; Mori, K. J. Chem. Soc., Perkin Trans. 1 1991, 2919.
42. (d) Mori, K. Bull. Soc. Chim. Belg. 1992, 101, 393.
43. (e) Mori, K.; Matsushima, Y. Synthesis 1993, 406.
44. (f) Mori, K.; Matsushima, Y. Synthesis 1994, 417.
45. (f) Mori, K.; Matsushima, Y. Synthesis 1995, 845.
46. (a) Almquist, F.; Eklund, L.; Frejd, T. Synth. Commun. 1993, 23, 1499.
47. (b) Almquist, F.; Frejd, T. Tetrahedron: Asymmetry 1995, 6, 957.
48. (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J Org. Chem. 1969, 34, 2543.
49. (b) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
50. (c) Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165.
51. Crabbé, P. Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry; Holden-Day: San Francisco, 1965; pp 232-237.
52. (a) Koft, E. R. Tetrahedron 1987, 43, 5775.
53. (b) Neunert, D.; Klein, H.; Welzel, P. Tetrahedron 1989, 45, 661.
54. Geribaldi, S ; Torri, G.; Azzaro, M. Bull. Soc. Chim. Fr. 1973, 2836.