One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides.
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DOI: 10.1016/j.carres.2016.11.018
Abstract: 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… read more here.
Keywords: ferrier rearrangement; chromanone glycosides; rearrangement glycals; one pot ... See more keywords
Silicon-Assisted Ferrier Rearrangement in Preparation of C3-Silyl Glycosides.
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DOI: 10.1021/acs.orglett.5c04215
Abstract: Herein, we report a Lewis acid catalyzed Ferrier rearrangement glycosylation strategy using the α-effect of C3-silylated glucal donors. The dimethylphenylsilyl group at the C3 position promotes the reaction where the unactivated free hydroxy group at… read more here.
Keywords: assisted ferrier; silyl glycosides; silicon assisted; ferrier rearrangement ... See more keywords
Diastereoselective Synthesis of C-Vinyl Glycosides via Gold(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Ferrier Rearrangement.
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DOI: 10.1021/acs.orglett.7b03062
Abstract: A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the involvement… read more here.
Keywords: vinyl glycosides; ferrier rearrangement; acyloxy migration; gold ... See more keywords
Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Brønsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement.
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DOI: 10.1021/acs.orglett.9b00009
Abstract: An acidity- and temperature-dependent chemoselective glycosylation of silyl-protected rhamnals with alcohols has been revealed. The reaction undergoes a 1,2-addition pathway with (±)-CSA as the catalyst at rt, affording kinetically controlled 2-deoxyl rhamnosides. In contrast, only… read more here.
Keywords: ferrier rearrangement; temperature; silyl protected; thermodynamically controlled ... See more keywords