Synthesis of chiral [60]fullerene-steroid bisadducts using steroid templates

Tetrahedron

Volumn 55, Issue 43, 1999, Pages 12515-12530

  Ishi i, Tsutomu ^a   Shinkai, Seiji ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; STEROID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; ISOMERISM; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTRAL SENSITIVITY; SYNTHESIS;

EID: 0033595886     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00742-5     Document Type: Article

References (39)

1. a) Nierengarten, J.-F.; Schall, C.; Nicoud, J.-F. Angew. Chem. Int. Ed. Engl., 1998, 37, 1934-1936.
2. b) Bourgeois, J.-P.; Echegoyen, L.; Fibbioli, M.; Pretsch, E.; Diederich, F. Angew. Chem. Int. Ed. Engl., 1998, 37, 2118-2121.
3. c) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta, 1998, 81, 1835-1844.
4. a) Nierengarten, J.-F.; Schall, C.; Nicoud, J.-F.; Heinrich, B.; Guillon, D. Tetrahedron Lett., 1998, 39, 5747-5750.
5. b) Cardullo, F.; Diederich, F.; Echegoyen, L.; Habicher, T.; Jayaraman, N.; Leblanc, R. M.; Stoddart, J. F.; Wang, S. Langmuir, 1998, 14, 1955-1959.
6. a) Nierengarten, J.-F.; Herrmann, A.; Tykwinski, R. R.; Rüttimann, M.; Diederich, F.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M. Helv. Chim. Acta, 1997, 80, 293-316.
7. b) Nierengarten, J.-F.; Felder, D.; Nicoud, J.-F. Tetrahedron Lett., 1999, 40, 269-272.
8. c) Taki, M.; Takigami, S.; Watanabe, Y.; Nakamura, Y.; Nishimura, J. Polym. J., 1997, 29, 1020-1022.
9. For review see: Diederich, F.; Kessinger, R. Acc. Chem. Res., 1999, 32, 537-545.
10. Nierengarten, J.-F.; Gramlich, V.; Cardullo, F.; Diederich, F. Angew. Chem. Int. Ed. Engl., 1996, 35, 2101-2103.
11. Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta, 1997, 80, 2238-2276.
12. Nierengarten, J.-F.; Felder, D.; Nicoud, J.-F. Tetrahedron Lett., 1998, 39, 2747-2750.
13. Nakamura, E.; Isobe, H.; Tokuyama, H.; Sawamura, M. Chem. Commun., 1996, 1747-1748.
14. Isobe, H.; Tokuyama, H.; Sawamura, M.; Nakamura, E. J. Org. Chem., 1997, 62, 5034-5041.
15. Taki, M.; Sugita, S.; Nakamura, Y.; Kasashima, E.; Yashima, E.; Okamoto, Y.; Nishimura, J. J. Am. Chem. Soc., 1997, 119, 926-932.
16. Ishi-i, T.; Nakashima, K.; Shinkai, S. Chem. Commun., 1998, 1047-1048.
17. Ishi-i, T.; Nakashima, K.; Shinkai, S.; Ikeda, A. J. Org. Chem., 1999, 64, 984-990.
18. Ishi-i, T.; Iguchi, R.; Shinkai, S. Tetrahedron, 1999, 55, 3883-3892.
19. Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem. Int. Ed. Engl., 1993, 32, 78-80.
20. 1H NMR spectra should be broadened due to the slow slipping motion around the cyclohexene rings in the open adducts. In the mass spectra of 11-13, the parent ion peaks for the open adducts were scarcely observed. In contrast, the mass spectrum of 10 afforded the parent ion peaks in the region of the open mono- and bisadducts, although the intensities of the peaks were relatively weak. The foregoing findings imply that the cyclic bisadduct of 10 is less stable than those of 11-13.
21. 1H NMR spectrum of 10, which gave the 6-7 proton peaks with same intensity for the COOMe group indicating the formation of the 6-7 isomers of 10
22. Hirsch, A.; Lamparth, I.; Karfunkel, H. R. Angew. Chem. Int. Ed. Engl., 1994, 33, 437-438.
23. a) Schick, G.; Hirsch, A.; Mauser, H.; Clark, T. Chem. Eur. J., 1996, 2, 935-943.
24. b) Djojo, F.; Herzog, A.; Lamparth, I.; Hampel, F.; Hirsch, A. Chem. Eur. J., 1996, 2, 1537-1547.
25. Taki, M.; Nakamura, Y.; Uehara, H; Sato, M.; Nishimura, J. Enantiomer, 1998, 3, 231-239.
26. For review see: Thilgen, C.; Diederich, F. Top. Curr. Chem., 1999, 199, 135-171.
27. a) Hawkins, J. M.; Meyer, A.; Nambu, M. J. Am. Chem. Soc., 1993, 115, 9844-9845.
28. b) Herrmann, A.; Rüttimann, M.; Thilgen, C.; Diederich, F. Helv. Chim. Acta, 1995, 78, 1673-1704.
29. c) Gross, B.; Schurig, V.; Lamparth, I.; Herzog, A.; Djojo, F.; Hirsch, A. Chem. Commun., 1997, 1117-1118.
30. d) Djojo, F.; Hirsch, A. Chem. Eur. J., 1998, 4, 344-356.
31. fC)-pattern.
32. The Cotton effects due to induced CD were found in some [60]fullerene derivatives having a chiral substituent. For example: a) Bianco, A.; Maggini, M.; Scorrano, G.; Toniolo, C.; Marconi, G.; Villani, C.; Prato, M. J. Am. Chem. Soc., 1996, 118, 4072-4080.
33. b) Wilson, S. R.; Lu, Q.; Cao, J.; Wu, Y.; Welch, C. J.; Schuster, D. I. Tetrahedron, 1996, 52, 5131-5142.
34. Recently, Diederich and his co-workers reported that the Cotton effects in cis-2 [60]fullerene-bisadducts with a chiral template were too weak to be detected (see ref. 6). It was concluded that the chiral template in the cis-2 bisadducts is too far from the achiral fullerene chromophore to generate the induced CD. The cis-2 bisadducts had only two chiral centers in the template part, however, the contribution of the number of the chiral centers was not discussed.
35. a) Yoshida, Z.; Takemura, H.; Takekura, S.; Matsubara, Y. Angew. Chem. Int. Ed. Engl., 1994, 33, 1597-1599.
36. b) Marconi, G.; Mayer, B. Pure Appl. Chem., 1997, 69, 779-783.
37. Takenaka, S.; Yamashita, K.; Takagi, M.; Hatta, T.; Tsuge, O. Chem. Lett., 1999, 319-320 and references cited therein.
38. Belik, P.; Gügel, A.; Kraus, A.; Walter, M.; Müllen, K. J. Org. Chem., 1995, 60, 3307-3310.
39. Malik, A. A.; Sharts, C. M. J. Fluorine Chem., 1987, 34, 395-408.