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
Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.
TL;DR: Aryl ether C- glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0) to create highly substituted tetrahydrofurans.
Journal ArticleDOI
InBr3-catalyzed Ferrier rearrangement: An efficient synthesis of C-pseudoglycals
TL;DR: Glycals react smoothly with silyl nucleophiles such as allyltrimethylsilane, trimethylsilyl cyanide and trimethyl-silylsilyl azide in the presence of a catalytic amount of indium tribromide to give the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycoly azides in excellent yields with high α-selectivity as mentioned in this paper.
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A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst
Bala Kishan Gorityala,Shuting Cai,Rujee Lorpitthaya,Jimei Ma,Kalyan Kumar Pasunooti,Xue-Wei Liu +5 more
TL;DR: A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system and phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glycal to 2,3-unsaturated O-glycosides.
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A facile Er(OTf)3-catalyzed synthesis of 2,3-unsaturated O- and S-glycosides.
Antonio Procopio,Renato Dalpozzo,Antonio De Nino,Loredana Maiuolo,Monica Nardi,Manuela Oliverio,Beatrice Russo +6 more
TL;DR: Er(OTf)(3) is a useful catalyst for the Ferrier rearrangement furnishing high yields of O- and S-glycosides and the catalyst, which is also commercially available, can be recovered and reused.
Journal ArticleDOI
Stereoselective synthesis of α-glucosides from 3-O-propargyl protected glucal exploiting the alkynophilicity of AuCl3
Sudhir Kashyap,Srinivas Hotha +1 more
TL;DR: In this paper, the synthesis of 2,3-unsaturated α-d -glucosides by the S N 2′ addition of diverse aglycones onto 4,6-di-O -benzyl-3- O -propargyl glucal was achieved using a catalytic quantity of AuCl 3.
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Stereoselective palladium-catalyzed O-glycosylation using glycals
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