Sugar-derived aziridines: Functionalization via lithiation of the aziridine ring

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1181-1182

  Bisseret, Philippe ^a   Bouix Peter, Claire ^a   Jacques, Olivier ^a   Henriot, Stéphanie ^a   Eustache, Jacques ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001562986     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990841e     Document Type: Article

References (15)

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2. (b) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799-802.
3. (c) Paulsen, H.; Matzke, M.; Orthen, B.; Nuck, R.; Reutter, W. Liebigs Ann. Chem. 1990, 953-963.
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5. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687.
6. The thermal decomposition of olefinic azides is still not well understood and may yield mixtures of products; see for instance: (a) Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-753.
7. (b) Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958.
8. (c) Krülle, T. M.; dela Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. K.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820.
9. Vedejs, E.; Kendall, J. T. J. Am. Chem. Soc. 1997, 119, 6941-6942.
10. Bouix, C.; Bisseret, P.; Eustache, J. Tetrahedron Lett. 1998, 39, 825-828.
11. (a) Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chem. Acta 1991, 74, 2073-2077.
12. (b) Alper, P. B.; Hung, S-C.; Wong, C.-H. Tetrahedron Lett. 1996, 34, 6029-6032. The thermal lability of azide 4 (previously prepared once by another route) has been noted: Pearson, W. H.; Hines, V. A. Tetrahedron Lett. 1991, 32, 5513-5516.
13. (b) Alper, P. B.; Hung, S-C.; Wong, C.-H. Tetrahedron Lett. 1996, 34, 6029-6032. The thermal lability of azide 4 (previously prepared once by another route) has been noted: Pearson, W. H.; Hines, V. A. Tetrahedron Lett. 1991, 32, 5513-5516.
14. Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403-406.
15. 3 complexes, 7c was directly obtained as a free, noncomplexed aziridine. We attribute the difference between the stability of complexes 7a,b and that of 7c to reduced electron density on the nitrogen atom in the latter case.