Electrochemical\nFerrier Rearrangement of Glycals

The\nFerrier rearrangement (FR) is a well-documented reaction\nthat\nrelies on strong acids or oxidants to convert glycals into unsaturated\nglycosyl derivatives. In this work, we introduce an electrochemical\nvariant of the FR, offering a broad substrate compatibility. Various\nnucleophiles and glycal derivatives afford 2,3-unsaturated glycosyl\nderivatives in high yields with excellent diastereoselectivities.\nThis sustainable method promises to expand the electrochemistry applications\nin sugar chemistry.

Publication Details

Journal
Figshare
Published
2024-10-21
DOI
https://doi.org/10.1021/acs.orglett.4c03511.s001
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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Electrochemical\nFerrier Rearrangement of Glycals

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Carbohydrate Chemistry and Synthesis
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Electrochemical\nFerrier Rearrangement of Glycals

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Abstract

The\nFerrier rearrangement (FR) is a well-documented reaction\nthat\nrelies on strong acids or oxidants to convert glycals into unsaturated\nglycosyl derivatives. In this work, we introduce an electrochemical\nvariant of the FR, offering a broad substrate compatibility. Various\nnucleophiles and glycal derivatives afford 2,3-unsaturated glycosyl\nderivatives in high yields with excellent diastereoselectivities.\nThis sustainable method promises to expand the electrochemistry applications\nin sugar chemistry.

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Carbohydrate Chemistry and Synthesis
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Electrochemical\nFerrier Rearrangement of Glycals · Figshare (2024) | TGRS Research Map | TGRS