Cardiff University | Prifysgol Caerdydd ORCA
Online Research @ Cardiff 
WelshClear Cookie - decide language by browser settings

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 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

Full text not available from this repository.

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: 04 Jun 2017 02:54
URI: http://orca.cf.ac.uk/id/eprint/13480

Citation Data

Cited 8 times in Google Scholar. View in Google Scholar

Cited 9 times in Scopus. View in Scopus. Powered By Scopus® Data

Cited 7 times in Web of Science. View in Web of Science.

Actions (repository staff only)

Edit Item Edit Item