Bis-Benzyl Protected 6-Amino Cyclitols are Poisenous to Pd/C Catalysed Hydrogenolysis of Benzyl Ethers

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Pd/C and Pd(OH)(2)/C catalysts are both poisoned by bis-benzyl protected 6-aminocyclitols thereby inhibiting the hydrogenolysis of benzyl ethers but removing N-Cbz groups chemoselectively. This outcome was unaltered by the use of different hydrogen donors. Replacement of the C-6 nitrogen atom by oxygen resulted in the starting materials being fully deprotected under similar conditions. These findings add cyclitolamines to the list of amines/bases that are poisonous to Pd/C catalysts during hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.


Original languageEnglish
Pages (from-to)1223-1226
Number of pages4
JournalTetrahedron Letters
Publication statusPublished - 2 Feb 2004


  • catalysis, poison, deprotection