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Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives

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Glycoscience

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 215))

Abstract

Glycals (or usually their O-substituted derivatives) are readily converted into 2,3-unsaturated glycosyl compounds with O-, C-, N-, S- or otherwise linked substituents at the anomeric position. These products have been found to be useful for a range of synthetic purposes. In particular, the C-glycosidic compounds have served as readily available starting materials for the preparation of useful non-carbohydrate compounds. While these allylic rearrangement processes are usually conducted under the influence of Lewis acid catalysts, adaptations that involve activation of the allylic substituents of the starting glycals as leaving groups under neutral conditions have been developed. General features of the reactions are described as well as applications in synthesis and extensions of the basic processes.

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  1. Industrial Research, PO Box 31-310, Lower Hutt, New Zealand

    Robert J. Ferrier

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  1. Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, 8010, Graz, Austria

    Arnold E. Stütz

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Ferrier, R.J. (2001). Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives. In: Stütz, A.E. (eds) Glycoscience. Topics in Current Chemistry, vol 215. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-44422-X_7

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  • DOI: https://doi.org/10.1007/3-540-44422-X_7

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