Issue 29, 2012

Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols

Abstract

A temperature-controlled mechanism switch between the Al(OTf)3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.

Graphical abstract: Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols

Supplementary files

Article information

Article type
Paper
Submitted
13 Mar 2012
Accepted
06 Jun 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 5636-5642

Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols

D. B. G. Williams, S. B. Simelane and H. H. Kinfe, Org. Biomol. Chem., 2012, 10, 5636 DOI: 10.1039/C2OB25540E

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