Bis-benzyl protected 6-amino cyclitols are poisonous to Pd/C catalysed hydrogenolysis of benzyl ethers |
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Authors: | M Bashir-Uddin Surfraz |
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Affiliation: | School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK |
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Abstract: | 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. |
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Keywords: | Catalysis Deprotection Poison |
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