Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
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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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Silica gel enables Achmatowicz rearrangement with KBr/oxone under “anhydrous” condition for one-pot functionalization
Guodong Zhao,Rongbiao Tong +1 more
TL;DR: This new protocol allows direct functionalization of AchR products in a one-pot manner, effectively reducing the cost, time, and environmental impacts derived from the conventional stop-and-go approach using separate reaction vessels.
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Diastereoselective Synthesis of C-Vinyl Glycosides via Gold(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Ferrier Rearrangement
TL;DR: 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.
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Zn(II) Triflate-Catalyzed N-Glycosylation: Synthesis of Sulfonamide and Amide Functionalized 2,3-Unsaturated Glycosides
TL;DR: A highly efficient and mild method for the synthesis of glycosyl sulfonamides andglycosyl amides from glycal has been described using Zn(OTf)2 as an economical and environmentally friendly catalyst.
Journal ArticleDOI
Open-Air Stereoselective Construction of C-Aryl Glycosides.
Mengnan Lai,Karwan Abdulmajed Othman,Karwan Abdulmajed Othman,Hui Yao,Qiuyuan Wang,Feng Yongkui,Nianyu Huang,Ming-Guo Liu,Kun Zou +8 more
TL;DR: A new methodology of stereoselective C-glycosylation has been developed with 3,4-O-carbonate glycals and boronic acids, catalyzed by 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate under open-air conditions at room temperature.
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Sequential glycosylation/endo-dig cyclization of sugar enynones for the synthesis of pyrano[3,2-c]furan scaffolds
TL;DR: In this paper, a sugar derived enynones undergo a sequential glycosylation/endo-dig cyclization with alcohols under the influence of 10 ǫ% AgSbF 6 and a stoichiometric amount of NaHCO 3 in dichloromethane at 0 ÁC to afford a novel class of sugar annulated furan scaffolds in good yields.
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.
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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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