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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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.
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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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Journal ArticleDOI
Synthesis of diastereoisomeric 6-deoxy-d-allal- and 6-deoxy-d-galactal-derived allyl epoxides and examination of the regio- and stereoselectivity in nucleophilic addition reactions. Comparison with the corresponding 6-O-functionalized allyl epoxides
TL;DR: The reaction of 8α and 8β with azide (TMSN 3, N -nucleophile) made it possible to revise a previously proposed rationalization for the formation of the corresponding cis-azido alcohol (syn -1,2-addition product) as mentioned in this paper.
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Ferric Sulphate Hydrate–Catalyzed, Microwave‐Assisted Synthesis of 2,3‐Unsaturated O‐Glycosides via the Ferrier Reaction
Guisheng Zhang,Qingfeng Liu +1 more
TL;DR: Fe2(SO4)3···xH2O catalyzes the Ferrier reaction of per−O−acetylated/benzylated glycals with alcohols to give 2,3−unsaturated α−glycosides in a few minutes under microwave irradiation as mentioned in this paper.
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Straightforward route to 2- and 3-formyl hex-1- and -2-enopyranosides and their highly stereoselective hetero Diels–Alder reaction with ethyl vinyl ether
TL;DR: In this paper, a straightforward route from D-glucose to conjugated enal and diene pyranoses through a dithiane-based methodology is disclosed; hetero Diels-Alder reaction of the enals with ethyl vinyl ether occurs with high stereoselectivity.
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Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst
TL;DR: In this paper, the combination of α-zirconium sulfophenylphosphonate-methanphosphoneate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.
Journal ArticleDOI
An efficient method for the selective synthesis of 2-deoxy-2-iodo-glycosides by O-glycosidation of d-glucal using I2–Cu(OAc)2
TL;DR: An efficient and convenient method for the synthesis of 2-deoxy-2-iodo- O-glycosides from tri-O-acetyl-D-glucal with various alcohols by using I₂-Cu(OAc)₁ is described.
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