Intramolecular thiol-yne cyclisation as a novel strategy for thioglycal synthesis

A novel intramolecular thiol-yne cyclisation strategy has been developed for the synthesis of thioglycals. Both ionic and radical mediated cyclisation pathways have been investigated for D- and L-sugars. The ionic cyclisation provides exclusive access to 5-exo products directly from the thioesters w...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-05, Vol.51 (41), p.8672-8674
Main Authors: Corcé, Vincent, McSweeney, Lauren, Malone, Aoife, Scanlan, Eoin M
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Cyclization
Glycosides - chemical synthesis
Glycosides - chemistry
Irradiation
Molecular Conformation
Pathways
Photochemical
Radicals
Strategy
Sulfhydryl Compounds - chemistry
Synthesis
Thioesters
Thiols
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Summary:A novel intramolecular thiol-yne cyclisation strategy has been developed for the synthesis of thioglycals. Both ionic and radical mediated cyclisation pathways have been investigated for D- and L-sugars. The ionic cyclisation provides exclusive access to 5-exo products directly from the thioesters whereas the radical cyclisation provides access to both 5-exo and 6-endo products upon photochemical irradiation of the free thiols. These are the first examples of intramolecular thiol-yne cyclisation reactions applied to thiosugar synthesis.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc02162f