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
Methods for 2-Deoxyglycoside Synthesis.
Clay S. Bennett,M. Carmen Galan +1 more
TL;DR: This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter.
Journal ArticleDOI
Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals
TL;DR: This review highlights the C-glycosylation methods that have been practised in the total synthesis of natural products and pharmaceuticals in the past decade.
Journal ArticleDOI
Recent developments in β-C-glycosides: synthesis and applications
Krishnamoorthy Lalitha,Kumarasamy Muthusamy,Y. Siva Prasad,Praveen Kumar Vemula,Subbiah Nagarajan +4 more
TL;DR: In the last few years, considerable progress has been made in the synthesis of C-glycosides as mentioned in this paper, and due to its versatility, C glycosides play a pivotal role in developing novel materials, surfactants and bioactive molecules.
Journal ArticleDOI
Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone
Igor V. Alabugin,Leah Kuhn,Michael G. Medvedev,Michael G. Medvedev,Nikolai V. Krivoshchapov,Nikolai V. Krivoshchapov,Vera A. Vil,Ivan A. Yaremenko,Patricia Mehaffy,Meysam Yarie,Alexander O. Terent'ev,Mohammad Ali Zolfigol +11 more
TL;DR: In this article, the authors evaluate the fundamental connections between the anomeric effect and a broad variety of O-functional groups and highlight the vast implications of AE for the structure and reactivity of organic O-functionalities.
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Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
TL;DR: This review summarizes the literature on the different transformations of the endo glycals into biologically relevant compounds as well as on the use of glycals as chiral building blocks for the synthesis of various natural products such as aspicilin, reblastatin, diospongins, decytospolides, osmundalactones, paclitaxel, isatisine, d-fagomine, and spliceostatin, reported post 2014.
References
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Journal ArticleDOI
Synthesis of 2,3-unsaturated glycopyranosides by Ferrier rearrangement in FeCl3 based ionic liquid
Rutuja D. Tilve,M. Varughese Alexander,Amit C. Khandekar,Sriniwas D. Samant,Vinod R. Kanetkar +4 more
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.
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Iodine-catalyzed Ferrier Reaction 1. A Mild and Highly Versatile Glycosylation of Hydroxyl and Phenolic Groups1
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Über neue Reduktionsprodukte des Traubenzuckers: Glucal und Hydro-glucal
TL;DR: In this paper, a Tetraacetyl-Derivat des Sorbits entstehe in reichlicher Menge ein gut krystalli-sierender Korper, der nach der Analyse, Molekulargewichtsbestimmung und dem Resultat der Hydrolyse die Formel C12H16O7 hat.
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An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement
TL;DR: In this article, 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.
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The acid-catalysed reaction of thiols with alkyl 2,3-dideoxy-glyc-2-enopyranosides or glycals
TL;DR: A rationalization of the substitution reactions of 1,2- and 2,3-unsaturated sugars based on HSAB principle has been proposed in this article, where cross experiments have confirmed the intermediacy of the allylic carbocation in the reaction.
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Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more