Abstract
Debenzylation by catalytic transfer hydrogenation (CTH) of various organic compounds is a simple, fast, and safe method. Though CTH is widely used in reductions, only few data are available for the conversion of azides to amines. The number of usable transfer compounds is limited in cases of sugar derivatives, as the most common transfer materials, e.g. hydrazine hydrate or formic acid, can compete in side-reactions. The present study explores the limits of the reaction parameters and transfer compounds.
Similar content being viewed by others
References
R.C. Petter and J.S. Salek:J. Am. Chem. Soc. 112, 3860 (1990).
R.L. Whistler, M.L. Wolfrom, and J.N. BeMiller (eds.):Methods in Carbohydrate Chemistry, Academic Press, N.Y.-London, Volume 2, p. 321 and Volume 1, p. 119 (1963).
T. Bieg and W. Szeja:Synthesis 76 (1985).
T. Gartisier, C. Sleva, and J.J. Delmoch:Tetrahedron Lett. 24, 1609 (1983).
S. Ram and R.E. Elvenkampfer:Synthesis 91 (1988).
E.F.V. Scriven and K. Turnbull:Chem. Rev. 88, 298 (1988).
S.W. Weller:Catal. Rev.-Sci. Eng. 34, 227 (1992).
E. Tóth, J. Törley, and B. Hegedüs: EP-A-0412820 (1990).
Author information
Authors and Affiliations
Additional information
Dedicated to Professor József Szejtli.
Rights and permissions
About this article
Cite this article
Jicsinszky, L. Catalytic transfer hydrogenation of cyclodextrin azides and benzylated glucose derivatives. J Incl Phenom Macrocycl Chem 18, 247–254 (1994). https://doi.org/10.1007/BF00708731
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00708731