Indium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1-->4)-C-disaccharides.

Abstract

Starting from methyl 6-bromo-4,6-dideoxy-alpha-D-threo-4-enopyranoside, 4-C-branched sugars have been prepared through indium-promoted Barbier-type allylation of various aldehydes in aqueous media followed by hydroboration of the resulting double bond. The intermediate unsaturated monosaccharides were shown to rearrange in acidic media to give 4-C-acetyl-5… (More)

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@article{Levoirier2004IndiumpromotedBA, title={Indium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1-->4)-C-disaccharides.}, author={Eric Levoirier and Yves Canac and St{\'e}phanie Norsikian and Andr{\'e} Lubineau}, journal={Carbohydrate research}, year={2004}, volume={339 17}, pages={2737-47} }