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
Stereoselective propargylation of glycals with allenyltributyltin(IV) via a Ferrier type reaction
TL;DR: In this paper, the introduction of an unsubstituted propargyl group to various glycals was achieved using a Ferrier type reaction with allenyltributyltin(IV).
Journal ArticleDOI
Scandium Triflate Catalyzed Thioglycosidation of Glycals: A Facile Synthesis of 2,3-Unsaturated Thioglycopyranosides
TL;DR: Scandium triflate was found to be an efficient Lewis acid for the thioglycosidation of 3,4,6-tri-O-acetyl or benzoyl-d-glycals with various thiols as discussed by the authors.
Journal ArticleDOI
Stereoselective synthesis of 2,3-unsaturated 1,6-oligosaccharides by means of a glycal-derived allyl epoxide and N-nosyl aziridine.
TL;DR: Synthetized 4-deoxy-4-amino-alpha-D-erythro-hex-2-enopyranosyl di- and trisaccharides of types A and B were synthetized by means of a reiterative, completely stereoselective glycosylation process which makes use of the D-galactal-derived allyl epoxide 1beta and D-allal- derived allyl N-nosyl aziridine 2
Journal ArticleDOI
Er(OTf)3 as New Efficient Catalyst for the Stereoselective Synthesis of C-Pseudoglycals
Antonio Procopio,Renato Dalpozzo,Antonio De Nino,Monica Nardi,Beatrice Russo,Antonio Tagarelli +5 more
TL;DR: Er(OTf) 3 is a useful catalyst for the Ferrier rearrangement furnishing high yields of products, cleaner reaction profiles, short reaction times, mild reaction conditions, high stereoselectivity and recoverability of the catalyst which is also commercially available as mentioned in this paper.
Journal ArticleDOI
Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides
Abstract: Starting from alkyl α- d -4- O -methanesulphonylpent-2-eno glycero pyranosides 13a – c , nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a – c and 15a – c . An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl α- d -hex-2-eno erythro pyranoside derivatives 6a and 6b . On the contrary, starting from alkyl β- d -4- O -methanesulphonylpent-2-eno glycero pyranosides 21a – c , azides 22a – c were exclusively obtained, and subsequently converted into the corresponding amino derivatives 23a – c . The behaviour of β-anomers 21a – c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations.
Related Papers (5)
Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more