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Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes

Benning, R. K., Osborn, H. M. I. and Turkson, A. (2011) Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes. Tetrahedron: Asymmetry, 22 (1). pp. 109-116. ISSN 0957-4166

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To link to this item DOI: 10.1016/j.tetasy.2010.11.031


The Beckmann rearrangement is a useful reaction employed to provide access to amides from oxime substrates. Applied to cyclic structures, the Beckmann rearrangement leads to ring expansion and allows access to cyclic lactams. Our investigations focused upon the synthesis of glycoside-derived lactams from oxime precursors. In probing a range of conditions, we observed that 2,4,6-trichloro[1,3,5]triazine (TCT) was an effective and mild promoter of the rearrangement affording pyrano- and heptanoside lactam products with excellent regioselectivities.

Item Type:Article
Divisions:Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
ID Code:16536

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