Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes

Benning, R. K., Osborn, H. M. I. ORCID: https://orcid.org/0000-0002-0683-0457 and Turkson, A. (2011) Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes. Tetrahedron: Asymmetry, 22 (1). pp. 109-116. ISSN 0957-4166 doi: 10.1016/j.tetasy.2010.11.031

Abstract/Summary

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
URI	https://reading-clone.eprints-hosting.org/id/eprint/16536
Item Type	Article
Refereed	Yes
Divisions	Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
Publisher	Elsevier
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