Elsevier

Tetrahedron Letters

Volume 41, Issue 33, 12 August 2000, Pages 6403-6406
Tetrahedron Letters

Stereoselective synthesis of α-aminonitriles at non-anomeric positions of monosaccharides

https://doi.org/10.1016/S0040-4039(00)01090-XGet rights and content

Abstract

α-Aminonitriles have been stereoselectively introduced at non-anomeric positions of monosaccharides, in which the carbon C-α is one of the atoms of the sugar ring. Target compounds were prepared from various ulose derivatives and amines using titanium(IV) isopropoxide as a mild and effective Lewis acid.

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Acknowledgements

We thank the Conseil Régional de Picardie and the Ministère Français de la Recherche for financial support and G. Mackenzie for helpful discussions.

References (14)

  • Shafran, Yu. M.; Bakulev, V. A.; Mokrushin, V. S. Russ. Chem. Rev. 1989, 58,...
  • Brunner, H.; Hankofer, P.; Holzinger, U.; Treittinger, B.; Schönenberger, H. Eur. J. Med. Chem. 1990, 25,...
  • Gale, G. R.; Walker, E. M.; Atkins, L. M.; Smith, A. B.; Heischen, S. J. Res. Commun. Chem. Pathol. Pharmacol. 1974, 7,...
  • Velázquez, S.; Chamorro, C.; Pérez-Pérez, M. J.; Alvarez, R.; Jimeno, M. L.; Domenech, A. M.; Pérez, C.; De Clercq, E.;...
  • Balzarini, J.; Camarasa, M. J.; Karisson, A. Drugs of the Future 1993, 18,...
  • Marco, J. L.; Ingate, S. T.; Manzano, P. Tetrahedron Lett. 1998, 39,...
  • Marco, J. L.; Ingate, S. T. Tetrahedron Lett. 1997, 38,...
There are more references available in the full text version of this article.

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