An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation

An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation

The air- and water-stable iodonium salt phenyl­(trifluoro­ethyl)­iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require st...

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Veröffentlicht in:Organic letters 2014-03, Vol.16 (6), p.1780-1782
Hauptverfasser: Chu, An-Hsiang Adam, Minciunescu, Andrei, Montanari, Vittorio, Kumar, Krishna, Bennett, Clay S
Format: Artikel
Sprache:eng
Schlagworte:
Air
Gases
Glycosylation
Letter
Mesylates
Molecular Structure
Stereoisomerism
Thioglycosides - chemistry
Water
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Zusammenfassung:The air- and water-stable iodonium salt phenyl­(trifluoro­ethyl)­iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background to construct glycosidic linkages.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5004059