Resolution and absolute configuration of a C2-symmetric trans -2,5- disubstituted fulleropyrrolidine

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4187-4190

  Tan, Xuefei ^a   Schuster, David I ^a   Wilson, Stephen R ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIRCULAR DICHROISM; DIASTEREOISOMER; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0032508088     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00781-3     Document Type: Article

References (16)

1. 1. Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798.
2. 2. Wilson, S. R.; Wang, Y.; Cao, J.; Tan, X. Tetrahedron Lett. 1996, 37, 775.
3. 3. (a) Zhang, X.; Willems, M.; Foote, C. S. Tetrahedron Lett. 1993, 34, 8187.
4. (b) Shu, L.; Wang, G.; Wu, S.; Wu, H.; Lao, X. Tetrahedron Lett. 1995, 36, 3871.
5. (c) Iyoda, M.; Sultana, F.; Komatsu, M. Chem. Lett. 1995, 1133.
6. (d) Lawson, G. E.; Kitaygorodskiy, A.; Ma, B.; Bunker, C. E.; Sun, Y. J. Chem. Soc., Chem. Commun. 1995, 2225.
7. (e) Gan, L.; Zhou, D.; Luo, C.; Tan, H.; Huang, C.; Lu, M.; Pan, J.; Wu, Y.; J. Org. Chem. 1996, 61, 1954.
8. (f) Liou, K.; Cheng, C.; Chem. Commun. 1996, 1423.
9. (g) Averdung, J., Mattay, J. Tetrahedron 1996, 52, 5407
10. 4. Tsuge, O.; Kanemasa, S. Adv. Hetereocycl. Chem. 1989, 45, 231.
11. 5. Komori, A.; Kubota, M.; Ishida, T.; Niwa, H.; Nogami, T. Tetrahedron Lett, 1996, 37, 4031.
12. b = 11.6 for a normal N-methyl pyrrolidine.
13. 7. In general, we have also found that fulleropyrrolidine ureas are easily hydrolysed with acid, giving back the starting fulleropyrrolidine compounds.
14. 8. Wilson, S. R.; Lu, Q.; Cao, J.; Wu, Y.; Welch, C. J.; Schuster, D. I. Tetrahedron 1996,14, 5131.
15. 9. Hawkins, J. M.; Meyer, A.; Nambu, M. A J. Am. Chem. Soc. 1993, 115, 6548.
16. 10. Bianco, A.; Maggini, M.; Novello, F.; Toniolo, G.; Scorrano, G.; Villani, C.; Da Ros, T.; Prato, M. in "Fullerenes and Fullerene Nanostructures," Kuzmany, et. al., Eds, World Scientific, Singapore, 1996. Tetrahedron Letters 39 (1998) 4191-4194