Synthesis of 1, 3-oxazolidines from imines and epoxides catalyzed by samarium compounds

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3389-3393

  Nishitani, Takayuki ^a   Shiraishi, Hiroyuki ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

1, 3 oxazolidines; Catalytic synthesis; Epoxides; Imines; Samarium

Indexed keywords

EPOXIDE; IMINE; OXAZOLIDINE DERIVATIVE; SAMARIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034728959     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00374-9     Document Type: Article

References (19)

1. (a) Le Bail, M.; Perard, J.; Atiken, D. J.; Bonin, M.; Husson, H.-P. Tetrahedron Lett. 1997, 38, 7177-7180.
2. (b) Heaney, H.; Papageorgiou, G.; Wilkins, R. F. Tetrahedron 1997, 53, 14 381-14 396.
3. (a) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron: Asymmetry 1996, 7, 1245-1248.
4. (b) Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1997, 62, 3770-3771.
5. Bergman, E. D. Chem. Rev. 1953, 53, 309-352. Other useful methods are as follows.
6. Other useful methods are as follows: (a) Yli-Kauhaluoma, J. T.; Harwig, C. W.; Wentworth Jr., P.; Janda, K. D. Tetrahedron Lett. 1998, 39, 2269-2272.
7. (b) Polyak, F.; Dorofeeva, T.; Zelchans, G.; Shustov, G. Tetrahedron Lett. 1996, 37, 8223-8226.
8. (a) Shim, J.-G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 1053-1056.
9. (b) Letinois, S.; Dumur, J.-C.; Henin, F.; Muzart, J. Tetrahedron Lett. 1998, 39, 2327-2330.
10. (c) Henin, F.; Letinois, S.; Muzart, J. Tetrahedron Lett. 1997, 38, 7187-7190.
11. Shiraishi, H.; Kawasaki, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1996, 37, 7291-7294.
12. Shiraishi, H.; Nishitani, T. Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234-6238.
13. Shiraishi, H.; Nishitani, T.; Nishihara, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957-13964.
14. Frank, D.; Hee, C. European Patent Appl., 13 pp. (106:213933 CA).
15. + 204 (100), 162 (38), 91 (82), 70 (21).
16. 2 was prepared according to literature procedure: Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1981, 103, 6507-6508.
17. 2 with air: (a) Matsukawa, M.; Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 2101-2102.
18. (b) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3891-3894.
19. (c) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.