Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
TLDR
A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.About:
This article is published in European Journal of Organic Chemistry.The article was published on 2013-11-01. It has received 121 citations till now. The article focuses on the topics: Ferrier rearrangement & Ferrier carbocyclization.read more
Citations
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Journal ArticleDOI
Progress in the Synthesis of 2,3-unsaturated Glycosides
TL;DR: In this paper, a review summarizes recent advances in the application of various types of catalysts to Ferrier type-I rearrangement reactions, including their synthesis, mechanism, and application of 2, 3-unsaturated glycosides.
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Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis.
Irene Herrera-González,Elena M. Sánchez-Fernández,Abhijit Sau,Cristina Nativi,José M. García Fernández,M. Carmen Galan,Carmen Ortiz Mellet +6 more
TL;DR: Cooperative chiral phosphoric acid/Schreiner's thiourea organocatalysis proved better suited for generating 2-deoxy O-glycosides, significantly broadening the scope of the approach.
Journal ArticleDOI
Preparation of 2,3-unsaturated pseudoglycosides with Ferrier Rearrangement promoted by Tm(OTf)3 as a highly efficient catalyst
Peiran Chen,Bin Bi +1 more
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.
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Bismuth-Catalyzed Stereoselective 2-Deoxyglycosylation of Disarmed/Armed Glycal Donors.
TL;DR: Bi(OTf)3 promoted direct and highly stereoselective glycosylation of "disarmed" and "armed" glycals to synthesize 2-deoxyglycosides has been reported.
Journal ArticleDOI
Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides.
TL;DR: A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement, which successfully catalyzed a wide range of substrates under very mild reaction conditions.
References
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Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
TL;DR: A novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported, and the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1, 3-dipoles entering the reaction.
Journal ArticleDOI
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
TL;DR: In this article, a reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds.
Journal ArticleDOI
The growing impact of click chemistry on drug discovery.
TL;DR: The copper-(I)-catalyzed 1,2,3-triazole formation from azides and terminal acetylenes is a particularly powerful linking reaction, due to its high degree of dependability, complete specificity, and the bio-compatibility of the reactants.
Journal ArticleDOI
Click-Chemie: diverse chemische Funktionalität mit einer Handvoll guter Reaktionen
TL;DR: In this paper, the authors show how in der Natur am haufigsten vorkommenden Verbindungen, so fallt auf, dass the Bildung von Kohlenstoff-Heteroatom-Bindungen gegenuber der von KHO-Kohlenstoffs-KHO-Bindingsen deutlich bevorzugt is, and das Medium naturlicher Reaktionen zumeist Wasser ist.
Journal ArticleDOI
CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
TL;DR: An overview of the mechanism of this remarkable reaction is presented as a means to explain the myriad of experimental results, particularly the various methods of catalyst generation, solvent and substrate effects, and choice of base or ligand as discussed by the authors.
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Hahn Kim,Hongbin Men,Chulbom Lee +2 more