Chemoselective synthesis and resolution of chiral [1,9]methanofullerene[70] derivatives

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5198-5199

  Wang, Yihan ^a   Schuster, David I ^a   Wilson, Stephen R ^a   Welch, Christopher J ^b  

^a NEW YORK UNIVERSITY   (United States)

^b REGIS TECHNOLOGIES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000871606     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961070k     Document Type: Article

References (30)

1. Reviews: (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685. (b) Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 243. (c) Hirsch, A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994. (d) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem., in press.
2. Reviews: (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685. (b) Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 243. (c) Hirsch, A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994. (d) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem., in press.
3. Reviews: (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685. (b) Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 243. (c) Hirsch, A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994. (d) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem., in press.
4. Reviews: (a) Taylor, R.; Walton, D. R. M. Nature 1993, 363, 685. (b) Diederich, F.; Isaacs, L.; Philip, D. Chem. Soc. Rev. 1994, 243. (c) Hirsch, A. The Chemistry of the Fullerenes; Thieme Medical Publishers: New York, 1994. (d) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem., in press.
5. 70, see: (a) Taylor, R. J. Chem. Soc., Perkin Trans. 2 1993, 813. A new numbering system has been proposed by this author in which [1,9] = [1,2] and [7,8] = [5,6]; see: (b) Taylor, R. The Chemistry of Fullerene; World Scientific, Singapore, 1995; Until the new numbering system is widely accepted, we prefer to use the more common convention.
6. 70, see: (a) Taylor, R. J. Chem. Soc., Perkin Trans. 2 1993, 813. A new numbering system has been proposed by this author in which [1,9] = [1,2] and [7,8] = [5,6]; see: (b) Taylor, R. The Chemistry of Fullerene; World Scientific, Singapore, 1995; Until the new numbering system is widely accepted, we prefer to use the more common convention.
7. (a) Henderson, C. C.; Rohlfing, C. M.; Cahill, P. A. Chem. Phys. Lett. 1992, 213, 383.
8. (b) Karfunkel, H. R.; Hirsch, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 7468.
9. (c) Avent, A. G.; Durwish, A. D.; Heimbach, H. W.; Kroto, H. W.; Meidine, M. F.; Parson, J. P.; Remars, C.; Roers, R.; Ohashi, O.; Taylor, R.; Walton, D. M. R. J. Chem. Soc., Perkin Trans. 2 1994, 15.
10. (a) Hawkins, J. M.; Meyer, A.; Solow, M. A. J. Am. Chem. Soc. 1993, 115, 7499.
11. (b) Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Goldschmidt, R. J. J. Chem. Soc., Chem. Commun. 1994, 2187.
12. (c) Meier, M. S.; Poplawska, M.; Compton, A. L.; Shaw, J. P.; Selegue, J. P.; Guarr, T. F. J. Am. Chem. Soc. 1994, 116, 7044.
13. (d) Herrmann, A.; Diederich, F.; Thilgen, C.; Meer, H.-U.; Muller, W. H. Helv. Chim. Acta 1994, 77, 1689.
14. (e) Smith, A. B., III; Strongin, R. M.; Brard, L.; Furst, G. T.; Romanow, W. J.; Owens, K. G.; Goldschmidt, R. J.; King, R. C. J. Am. Chem. Soc. 1995, 117, 5492.
15. (f) Wilson, S. R.; Lu, Q. J. Org. Chem. 1995, 60, 6496.
16. (a) Hirsch, A.; Grosser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126, 1061.
17. (b) Bingel, C. Chem. Ber. 1993, 126, 1957.
18. (c) Meidine, M. F.; Avent, A. G.; Darwish, A. D.; Kroto, H. W.; Ohashi, O.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Perkin Trans. 2 1994, 1189.
19. (d) Zhang, X.-J.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 4271.
20. 70 gave at least four isomeric monoadducts: Wang, Y.; Schuster, D. I.; Wilson, S. R. Unpublished results.
21. Wang, Y.-H.; Cao, J.-R.; Schuster, D. I.; Wilson, S. R. Tetrahedron Lett. 1995, 36, 6843.
22. (a) Speziale, A. J.; Tung, C. C.; Ratts, K. W.; Yao, A. J. Am. Chem. Soc. 1965, 87, 3460.
23. (b) Ratts, K. W.; Yao, A. N. J. Org. Chem. 1966, 31, 1185.
24. Henderson, C. C.; Rohlfing, C. M.; Gillen, K. T.; Cahill, P. A. Science 1994, 264, 397.
25. 8 symmetry.
26. 2 The chirality is due to differences in ring size (5- vs 6-membered) on each side of the cyclopropane ring, which translates into differences in curvature on the surface. In a more global sense, the chirality is due to a "bulge" on one side of the fullerene core, as shown in Figure 1. (Equation Presented)
27. Pirkle, W. H.; Welch, C. J.; Lamm, B. J. Org. Chem. 1992, 57, 3856.
28. 60 derivatives. See: Wilson, S. R.; Lu, Q.; Cao, J.; Wu, Y.; Welch, C. J.; Schuster, D. I. Tetrahedron 1996, 52, 5131.
29. 70.
30. Isaacs, L.; Diederich, F. Helv. Chim. Acta 1993, 76, 2454.