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
More filters
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.
Journal ArticleDOI
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
More filters
Journal ArticleDOI
Reactions of difluoroenoxysilanes with glycosyl donors: synthesis of difluoro-C-glycosides and difluoro-C-disaccharides.
TL;DR: Application of this methodology to a xylose-derived acylsilane led to the formation of difluoro-C-disaccharides as an isosteric O-glycosyl mimetic.
Journal ArticleDOI
Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions: stereoselective synthesis of functionalized N-heterocycles
Adriano S. Vieira,Fernando P. Ferreira,Pedro F. Fiorante,Rafael C. Guadagnin,Hélio A. Stefani,Hélio A. Stefani +5 more
TL;DR: The stereoselective nucleophilic addition of potassium aryl- and alkynyltrifluoroborates to cyclic N-acyliminium ion derivatives from N-benzyl-3,4,5-triacetoxy-2- pyrrolidinone, affording the respective 5-substituted 2-pyrrolidsinone is described.
Journal ArticleDOI
Palladium-Catalyzed Stereoselective Formation of α-O-Glycosides
TL;DR: In this paper, a novel method for palladium-catalyzed stereoselective formation of α-O-glycosides has been developed, which relies on the palladium−biaryl phosphine catalyst−glycal donor complexation to control the anomeric selectivity.
Journal ArticleDOI
Bi(OTf)3 and SiO2-Bi(OTf)3 as effective catalysts for the Ferrier rearrangement.
TL;DR: Bi(OTf)3 and SiO2-Bi3 are found to effectively catalyze the Ferrier rearrangement of tri-O-acetyl glycals with different alcohols providing an effective route to 2,3-unsaturated O-glycosides with good anomeric selectivity and good to excellent yields after short reaction times.
Journal ArticleDOI
Ferrier sulfonamidoglycosylation of D-glycals
TL;DR: Two new glycosylsulfamides were tested as carbonic anhydrase (CA II) inhibitors and showed good properties in the micromolar range.
Related Papers (5)
Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more