Issue 29, 2012
From the journal:

Organic & Biomolecular Chemistry

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

D. Bradley G. Williams,*ab   Sandile B. Simelanea  and  Henok H. Kinfea  

* Corresponding authors

a Research Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, South Africa
E-mail: bwilliams@uj.ac.za
Fax: +2711 559 2819
Tel: +2711 559 3431

b Industrial Research Limited, 69 Gracefield Road, Lower Hutt, New Zealand
E-mail: b.williams@irl.cri.nz
Fax: +644 566 6004
Tel: +644 931 3421

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

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Article information

DOI
https://doi.org/10.1039/C2OB25540E
Article type
Paper
Submitted
13 Mar 2012
Accepted
06 Jun 2012
First published
13 Jun 2012

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

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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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