Topic
Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
Papers published on a yearly basis
Papers
More filters
TL;DR: In this paper, a metal-free catalytic system for synthesizing 2,3-unsaturated glycosides has been developed using a sulfuric acid/4 A molecular sieves, which can catalyze the reaction of 3,4,6-tri-O-acetyl-D-glucals and a wide range of alcohols at room temperature.
Abstract: A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a metal-free catalytic system. This catalyst, sulfuric acid/4 A molecular sieves can catalyze the reaction of 3,4,6-tri-O-acetyl-D-glucals and a wide range of alcohols at room temperature, affording 2,3-unsaturated glycosides in good α-selectivity (α/β > 6:1) via a Ferrier-type rearrangement.
8 citations
TL;DR: In this paper, 1-C-alkynyl sugars are prepared from 2-acetoxy-glucal triacetate and Dicobalt complexes of these sugar acetylenes can stabilize the anomeric carbenium cations, which promote the Ferrier-type rearrangement through the 5,6-dehydro precursors to afford alkynyl cyclohexanones after decomplexation.
8 citations
TL;DR: In this paper, an efficient Ferrier Rearrangement reaction system using Tm(OTf) 3 as the catalyst was established, and a series of O -, S -, N -, and C -2, 3-unsaturated-glucosides were obtained in good yields and high anomeric selectivities by the glycosidation of 3,4,6-tri-O -acetyl-d -glucal with the corresponding nucleophiles, including azaglycosylation with N -nucleophiles.
8 citations
TL;DR: In this paper, the reaction of tri-O-acetyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.
Abstract: The reaction of tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.
8 citations
TL;DR: In this paper, cyclic and linear peptides are O-glycosylated by 3-(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement.
8 citations