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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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.
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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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Convergent synthesis of fluoro and gem-difluoro compounds using trifluoromethyltrimethylsilane
TL;DR: In this article, the Brook rearrangement of the alcoholate adducts was used to give the corresponding difluoroenoxysilanes via the Brook reaction, leading to gem-difluoro functionalized derivatives in one-pot methodology.
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Synthesis of α-CF2-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides
TL;DR: A methodology allowing the synthesis alpha-CF(2)-mannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described, which converts into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.
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Synthesis of C-glycosides from glycals or vinylogous lactones and trimethylsilyl ketene acetals
TL;DR: In this paper, 2,3-Unsaturated C-glycosides were obtained in good to excellent yields from the trimethylsilyltriflate catalyzed reaction between carbohydrate derived cyclic enolethers (“glycals”) and trimethyl silyl ketene acetals; under similar conditions vinylogous lactones afforded the products of an 1,4-addition reaction.
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Use of Unsaturated Sugars as Alkylating Agents. Addition of Enol Esters and Ethers to Glycals
TL;DR: In this paper, enol esters were added to 1,5-anhydro-D-hex-1-enitols in the presence of a Lewis acid catalyst to yield 3-deoxy-α-Dhex-2-enopyranosyl compounds.
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Iron(III) triflate, a new efficient catalyst for Type I Ferrier Rearrangement
Peiran Chen,Shaoshan Wang +1 more
TL;DR: By using iron(III) triflate as catalyst, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been established in this article.
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