Unusual behaviour of aryl 2-deoxy-D-galactosides under Lewis acid catalysis: a facile entry to C-aryl 2-deoxy-D-glycosides and bridged chiral benzopyran derivatives
TL;DR: In this article, the unusual behavior of aryl 2-deoxy-D-galactopyranosides yielding two different products with BF 3 ·Et 2 O under different concentrations was reported.
About: This article is published in Tetrahedron Letters.The article was published on 1995-08-07. It has received 11 citations till now. The article focuses on the topics: Galactosides & Aryl.
Citations
More filters
175 citations
TL;DR: The exploration of this rearrangement of an O-aryl ether to an ortho-hydroxyaryl system under mild thermal and both Brønsted and Lewis acid-catalyzed conditions is discussed.
34 citations
TL;DR: A temperature-controlled mechanism switch between the Al(OTf)(3)-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented.
Abstract: A temperature-controlled mechanism switch between the Al(OTf)(3)-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.
28 citations
TL;DR: An unusual and facile approach for the synthesis of 2-benzofuranyl-3-hydroxyacetones from 6-acetoxy-β-pyrones and phenols is presented and the unexpected cascade event would provide new possible considerations in the β-pyrone-involved organic synthesis.
26 citations
TL;DR: Reported is the first organocatalytic asymmetric 1,3-alkyl shift in alkyl aryl ethers for the synthesis of chiral 3,3'-diaryloxindoles using a chiral Brønsted acid catalyst.
Abstract: Reported is the first organocatalytic asymmetric 1,3-alkyl shift in alkyl aryl ethers for the synthesis of chiral 3,3'-diaryloxindoles using a chiral Bronsted acid catalyst. Preliminary results showed that each enantiomer of the 3,3'-diaryloxindole, and a racemic mixture, showed different antiproliferative activities against HeLa cell lines by using an MTT assay.
21 citations
References
More filters
TL;DR: In this paper, an efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described.
Abstract: An efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described
189 citations
TL;DR: In this article, the use of Cp2HfCl2-AgClO4 in 1:2-ratio rather than 1:1-ration provides much higher reactivity for the activation of glycosyl fluoride.
125 citations
116 citations
84 citations
83 citations