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Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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TL;DR: Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6,tri-O-acetyl-D-glucal into 2,3,unsaturated O and S-glycosides via Ferrier rearrangement in moderate to excellent yields with high α selectivity as discussed by the authors.
11 citations
TL;DR: The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach.
11 citations
TL;DR: Au-catalyzed cycloisomerization of aryl propargyl ethers provides controlled transition from alkyne to carbonyl chemistry followed up by a Petasis-Ferrier rearrangement/aromatization cascade leading to substituted biaryls with functionalized naphthalene cores as mentioned in this paper.
11 citations
TL;DR: In this article, a general strategy for catalytic tin radical mediated, radical cascade reactions is proposed in which three rings are constructed in a single step, and the initial step in the tricyclisation process has been examined using 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides bearing unsaturated substituents at the 1-O and/or 4-O positions.
Abstract: A general strategy for catalytic tin radical mediated, radical cascade reactions is proposed in which three rings are constructed in a single step. The initial step in the tricyclisation process has been examined using 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides bearing unsaturated substituents at the 1-O and/or 4-O-positions. Substrates for cyclisation of substituents at the 1-O-position were prepared by a novel zinc chloride catalysed Ferrier rearrangement of tri-O-acetyl-D-glucal with unsaturated alcohols, whereas substrates for cyclisation of substituents at the 4-O-position were prepared by alkylation or acylation of ethyl 6-O-protected 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides. Propargyl substituents cyclise efficiently, but propenyl substituents less so. Propioloyl substituents undergo hydrostannylation without cyclisation.
10 citations
TL;DR: In this article, a series of 2,3-unsaturated glucosides have been synthesized from 3,4,6-tri-O-acetyl-d-glucal.
10 citations