An efficient method for the cleavage of aziridines using hydroxyl compounds

Tetrahedron Letters

Volumn 41, Issue 23, 2000, Pages 4677-4679

  Bhanu Prasad, B A ^a   Sekar, G ^a   Singh, Vinod K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; HYDROXYL GROUP;

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

EID: 0034640871     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00686-9     Document Type: Article

References (15)

1. (a) For a general review of aziridine chemistry, see: Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocylic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol 1a.
2. (b) Dauben, P.; Dubois, L.; Dau, M. E. T. H.; Dodd, R. H. J. Org. Chem. 1995, 60, 2035.
3. (c) da Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602.
4. (d) Bodenan, J.; Chanet-Ray, J.; Vessiere, R. Synthesis 1992, 288.
5. (e) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073.
6. (f) Nakajima, K.; Neya, M.; Yamada, S.; Okawa, K. Bull. Chem. Soc. Jpn. 1982, 55, 3049.
7. For Cr complex-catalyzed opening of aziridines with TMS azide, see: Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891.
8. For opening of aziridine with TMSCN in the presence of lanthanoid tricyanides, see: (a) Matsubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6379. (b) Osborn, H. M. I.; Sweeney, J. B. Synlett 1994, 145.
9. (b) Osborn, H. M. I.; Sweeney, J. B. Synlett 1994, 145.
10. For opening of aziridines with amines in the presence of Lewis acids, see: (a) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
11. (b) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395.
12. (c). Meguro, M.; Yamamoto, Y. Heterocycles 1996, 43, 2473.
13. For rearrangement of acylaziridines to oxazolines using orthogonal Lewis acids, see: Ferraris, D.; Drury III, W. J.; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
14. +).
15. 1H NMR spectra.