Showing papers on "Ferrier rearrangement published in 2004"
TL;DR: In this article, a novel and stereocontrolled glycosidation of 3,4,6-tri-O-acetyl-d-glucal with various alcohols to give the corresponding 2,3-unsaturated glycopyranosides using [bmim]Cl-1.5FeCl3 based ionic liquid is presented.
Abstract: A novel and stereocontrolled glycosidation of 3,4,6-tri-O-acetyl-d-glucal with various alcohols to give the corresponding 2,3-unsaturated glycopyranosides using [bmim]Cl–1.5FeCl3 based ionic liquid is presented. This ionic liquid has proved to be an efficient reaction medium, playing a dual role of a catalyst as well as of a solvent. Salient features of this simple methodology include non-hazardous reaction conditions, good yields in short reaction times and high anomeric selectivity.
58 citations
TL;DR: In this paper, the reaction of tri-O-acetyl-D-glucal with different nitrogen nucleophiles was effectively promoted by a catalytic amount of tris(pentafluorophenyl)borane for the first time in acetonitrile at room temperature to produce a variety of azapseudoglycals via Ferrier rearrangement.
43 citations
TL;DR: In this paper, the reaction of tri-O-acetyl-D-glucal with nucleophiles to afford the corresponding 2,3-unsaturated glycopyranosides in excellent yields by zirconium(IV) chloride in acetonitrile at ambient temperature has been demonstrated.
35 citations
TL;DR: InCl3 (2 mol%) in combination with Me3SiCl (20 mol%) efficiently catalyzes Ferrier rearrangement in a variety of glycal derivatives with different silyl nucleophiles to afford the corresponding Cpseudoglycals or unsaturated pyrans in nearly quantitative yields as discussed by the authors.
Abstract: InCl3 (2 mol%) in combination with Me3SiCl (20 mol%) efficiently catalyze Ferrier rearrangement in a variety of glycal derivatives with different silyl nucleophiles to afford the corresponding Cpseudoglycals or unsaturated pyrans in nearly quantitative yields. The stereoselectivities of the C-glycosides are good to excellent in favor of the α-anomers. A stoichiometric amount of InCl3 is necessary for similar transformations in the absence of Me3SiCl. The InCl3 can be recovered and reused without any loss of its activity.
14 citations
TL;DR: In this paper, the reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(lV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.
Abstract: The reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(lV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.
9 citations
TL;DR: In this article, the reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(lV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.
Abstract: The reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(lV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.
6 citations
TL;DR: In this article, the reaction of tri-O-acetyl-D-glucal with different nitrogen nucleophiles was effectively promoted by a catalytic amount of tris(pentafluorophenyl)borane for the first time in acetonitrile at room temperature to produce a variety of azapseudoglycals via Ferrier rearrangement.
Abstract: The reaction of tri-O-acetyl-D-glucal with different nitrogen nucleophiles was effectively promoted by a catalytic amount of tris(pentafluorophenyl)borane for the first time in acetonitrile at room temperature to produce a variety of azapseudoglycals via Ferrier rearrangement in good yields and preferential anomeric selectivity.