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Issue 29, 2012
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Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols

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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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Publication details

The article was received on 13 Mar 2012, accepted on 06 Jun 2012 and first published on 13 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25540E
Citation: 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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