Bis-benzyl protected 6-amino cyclitols are poisonous to Pd/C catalysed hydrogenolysis of benzyl ethers

Bashir-Uddin Surfraz, M., Akhtar, Mahmoud and Allemann, Rudolf Konrad ORCID: https://orcid.org/0000-0002-1323-8830 2004. Bis-benzyl protected 6-amino cyclitols are poisonous to Pd/C catalysed hydrogenolysis of benzyl ethers. Tetrahedron Letters 45 (6) , pp. 1223-1226. 10.1016/j.tetlet.2003.11.130

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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. 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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Catalysis; Deprotection; Poison
Publisher:	Elsevier
ISSN:	0040-4039
Last Modified:	18 Oct 2022 13:19
URI:	https://orca.cardiff.ac.uk/id/eprint/13480

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