One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides

One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto...

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Bibliographic Details
Published in:Carbohydrate research 2017-01, Vol.438, p.1-8
Main Authors: Dash, Ashutosh K., Madhubabu, Tatina, Yousuf, Syed Khalid, Raina, Sushil, Mukherjee, Debaraj
Format: Article
Language:English
Subjects:
2,3-Unsaturated glycosides
Acetophenones
Carbon - chemistry
Carbon-Ferrier rearrangement
Catalysis
Chromanone 3-C-glycosides
Chromans - chemistry
Glycopyranosides
Glycosylation
Lewis acid
Molecular Structure
Monosaccharides - chemistry
Stereoisomerism
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Summary:One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides. [Display omitted] •TBSOTf acts both as glycosylating and silylating agent.•In situ silylenol ether formation.•Avoidance of hazardous alkyl lithiums as strong base and cryogenic condition.•Highly stereoselective C-glycosylation.•Application in the syntheses of chromanone-3-C-glycosides.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2016.11.018