The Ferrier rearrangement (FR) is a well-documented reaction that relies on strong acids or oxidants to convert glycals into unsaturated glycosyl derivatives. In this work, we introduce an electrochemical variant of the FR, offering a broad substrate compatibility. Various nucleophiles and glycal derivatives afford 2,3-unsaturated glycosyl derivatives in high yields with excellent diastereoselectivities. This sustainable method promises to expand the electrochemistry applications in sugar chemistry.
Qi, C., Goti, G., Sartorel, A., Dell'Amico, L., Mazzarella, D. (2024). Electrochemical Ferrier Rearrangement of Glycals. ORGANIC LETTERS, 26(43), 9328-9333 [10.1021/acs.orglett.4c03511].
Electrochemical Ferrier Rearrangement of Glycals
Mazzarella, Daniele
2024-01-01
Abstract
The Ferrier rearrangement (FR) is a well-documented reaction that relies on strong acids or oxidants to convert glycals into unsaturated glycosyl derivatives. In this work, we introduce an electrochemical variant of the FR, offering a broad substrate compatibility. Various nucleophiles and glycal derivatives afford 2,3-unsaturated glycosyl derivatives in high yields with excellent diastereoselectivities. This sustainable method promises to expand the electrochemistry applications in sugar chemistry.| File | Dimensione | Formato | |
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