Photoinitiated thiol–ene mediated functionalisation of 4,5-enoses
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, <i>S</i>-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.
Authors
- Brendan Twamley
- Alejandro Prieto‐Castañeda (ORCID: https://orcid.org/0000-0002-7032-126X)
- Imlirenla Pongener (ORCID: https://orcid.org/0000-0002-1252-9396)
- Eoin M. Scanlan (ORCID: https://orcid.org/0000-0001-5176-2310)
- Harlei Martin (ORCID: https://orcid.org/0000-0002-6109-9855)
- Joshua T. McLean
- Gavin John Miller (ORCID: https://orcid.org/0000-0001-6533-3306)
- Laura Beswick (ORCID: https://orcid.org/0000-0002-1265-7742)
- Inés Rabadán González (ORCID: https://orcid.org/0009-0003-4611-8450)
- Tapasi Manna
Institutions
- Universidad Rey Juan Carlos (ES)
- Trinity College Dublin (IE)
- Keele University (GB)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00507h
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Science Foundation Ireland
- Irish Research Council
- Engineering and Physical Sciences Research Council