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Updated: May 20, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Photoinitiated thiol-ene mediated functionalisation of 4,5-enoses
Alejandro Prieto-Castañeda1,2, Harlei Martin1, Tapasi Manna3
1School of Chemistry & Trinity Biomedical Sciences Institute (TBSI), Trinity College Dublin, 152-160 Pearse Street, Dublin D02 R590, Ireland. eoin.scanlan@tcd.ie.
Abstract:
The photoinitiated thiol-ene reaction is emerging as a highly efficient methodology for thioglycoside synthesis. Herein, the radical-mediated hydrothiolation reaction of 4,5-unsaturated saccharides was extended, offering efficient access to C4-position, S-linked glycosides. A diverse range of 4,5-unsaturated saccharides were investigated with high-yields achieved for the thioether products with complete regioselectivity and good diastereoselectivity. 1,2-Ethanedithiol products furnished a thiol-residue suitable for tagging and fluorescent labelling of a disaccharide.
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