Highly Functionalized Cyclohexenyl Systems: Enzymatic Resolution and Selective Oxirane Opening Reactions of p-Benzoquinone Derivatives

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 5088-5093

  Kohrt, Jeffrey T ^a   Gu, Jian Xin ^a   Johnson, Carl R ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001445106     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980270o     Document Type: Article

References (45)

1. Johnson, C. R.; Adams, J. P.; Bis, S. J.; DeJong, R. L.; Golebiowski, A.; Medich, J. R.; Penning, T. D.; Senanayake, C. H.; Steensma, D. H.; Van Zandt, M. C. Pure Appl. Chem. 1992, 64, 1115.
2. Enzymatic asymmetrization: Johnson, C. R.; Haridrishnan, L. S.; Golebiowski, A. Tetrahedron Lett. 1994, 35, 7735.
3. Enzymatic resolution: Johnson, C. R.; Sakaguchi, H. Synlett 1992, 35, 6975.
4. (a) Johnson, C. R.; Miller, M. W. J. Org. Chem. 1995, 60, 6674.
5. (b) Johnson, C. R.; Miller, M. W. J. Org. Chem. 1997, 62, 1582.
6. (a) Lindstrom, U. M.; Franckowiak, R.; Pinault, N.; Somfai, P. Tetrahedron Lett. 1997, 38, 2027.
7. (b) Boaz, A. M. Tetrahedron Asymmetry 1995, 6, 15.
8. (c) Ross, A. M.; Pohl, T. M.; Piazza, K.; Thomas, M.; Fox, B.; Whalen, D. L. J. Am. Chem. Soc. 1982, 104, 1658.
9. (d) Taylor, R. J. K.; Haines, A. H.; Guo, Z.-X. Synlett 1993, 607.
10. (e) Hudlicky, T.; Luna, H.; Olivo, H. F.; Anderson, C.; Nugent, T.; Price, J. D. J. Chem. Soc. Perkin Trans. 1 1991, 2907
11. (f) Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
12. (f) Zipperer, B.; Hunkler, D.; Fritz, H.; Rihs, G.; Prinzbach, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 309.
13. (a) Tsuang, W.-S.; Griffin, G. W.; Horning, M. G.; Stillwell, W. G. J. Org. Chem. 1982, 47, 5339.
14. (b) Esser, T.; Farkas, F.; Mangholz, S.; Sequin, U. Tetrahedron, 1994, 50, 3709.
15. (c) Esser, T.; Sequin, U. Tetrahedron Lett. 1988, 29, 4405.
16. Lehmann, J.; Moritz, A. Carbohydr. Res. 1993, 239, 317.
17. Vogel, E.; Stegelmeier, H.; Altenbach, H. J. Tetrahedron Lett. 1978, 36, 3333.
18. Koreeda, M.; Yoshihara, M. J. Chem. Soc. Chem. Commun. 1981, 974.
19. (a) Crotti, P.; Bussolo, V. D.; Favero, L.; Pineschi, M. J. Org. Chem. 1996, 61, 9548.
20. (b) Crotti, P.; Bussolo, V. D.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537.
21. (c) Crotti, P.; Bussolo, V. D.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433.
22. (d) Crotti, P.; Bussolo, V. D.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1996, 37, 1675.
23. (e) Ohno, H.; Mori, A.; Inoue, S. Chem. Lett. 1993, 975.
24. Hudlicky, T.; Tian, X.; Konigsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037.
25. Muller, K.-H.; Kaiser, C.; Pillat, M.; Zipperer, B.; Froom, M.; Fritz, H.; Hunkler, D.; Prinzbach, H Chem. Ber. 1983, 116, 2492.
26. (a) Posner, G. H.; Angew. Chem., Intl. Ed. Engl. 1978, 17, 487.
27. (b) Nakajima, M.; Hasegawa, A.; Kurihara, N. J. Liebigs. Ann. 1965, 689, 235
28. (a) Jacobsen, E, N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773.
29. (b) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
30. (c) Leung, W.-H.; Chan, E. Y. Y.; Chow, E. K. F.; Williams, I. D. J. Chem. Soc., Dalton, Trans. 1996, 1229.
31. Bajaw, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021.
32. Kahre, D.; Yan, L. Synlett 1995, 523.
33. DeShong, P.; Pilcher, A. S. J. Org. Chem. 1993, 58, 5130.
34. (a) Tanner, D. Angnew. Chem. Intl. Ed. Engl. 1994, 33, 599.
35. (b) Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Ahang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681.
36. (c) Oguni, N.; Hoshimi, H.; Ono, K.; Hayashi, M Tetrahedron Lett. 1996, 52, 7817.
37. (d) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717.
38. (e) Hudlicky, T.; Olivo, H. F.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108.
39. Zamboni, R.; Rokach, J. Tetrahedron Lett. 1983, 24, 331.
40. Kametani, T.; Kigawa, Y.; Ihara, M. Tetrahedron 1979, 35, 313.
41. Hullar, T. L.; Baker, B. R. J. Org. Chem. 1965, 30, 4049.
42. (a) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575
43. (b) Larock, R. C.; Ding, S. J. Org. Chem. 1993, 58, 84.
44. (a) Trost, B. M.; Fortunak, J. M. J. Am. Chem. Soc. 1980, 102, 2841.
45. (b) Hauser, F. M.; Tommasi, R.; Hewawasam, P.; Rho, Y. S J. Org. Chem. 1988, 53, 4886.