Articles with "ferrier rearrangement" as a keyword



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

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Published in 2017 at "Carbohydrate research"

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
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Diastereoselective Synthesis of C-Vinyl Glycosides via Gold(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Ferrier Rearrangement.

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Published in 2018 at "Organic letters"

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
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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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Published in 2019 at "Organic letters"

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