Journal ArticleDOI
Synthesis of glycoside derivatives employing the ferrier rearrangement
Eusebius Wieczorek,Joachim Thiem +1 more
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TLDR
In this article, various glycals underwent smooth Lewis acid-catalysed allylic rearrangement reactions with O-nucleophiles to yield 2,3-unsaturated glycoside derivatives.About:
This article is published in Journal of Carbohydrate Chemistry.The article was published on 1998-05-01. It has received 30 citations till now. The article focuses on the topics: Ferrier rearrangement & Allylic rearrangement.read more
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Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
TL;DR: 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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Reference EntryDOI
Transformation of Glycals into 2,3‐Unsaturated Glycosyl Derivatives
Robert J. Ferrier,Oleg A. Zubkov +1 more
TL;DR: Various elimination procedures conducted on appropriate pyranoid and furanoid carbohydrate derivatives, especially on O-protected glycosyl halides afford cyclic vinyl ethers which Fischer (inappropriately) named glycals, form the major part of this chapter.
Journal ArticleDOI
(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides.
TL;DR: A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid, which acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides.
Related Papers (5)
Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more
Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal
R. J. Ferrier,N. Prasad +1 more