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

D. Bradley G. Williams; Sandile B. Simelane; Henok H. Kinfe

doi:10.1039/C2OB25540E

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Organic & Biomolecular Chemistry

Issue 29, 2012

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

D. Bradley G. Williams,*^a^b Sandile B. Simelane^a and Henok H. Kinfe^a

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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

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

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

DOI: 10.1039/C2OB25540E
Received 13 Mar 2012, Accepted 06 Jun 2012
First published online 13 Jun 2012

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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.

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

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