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Ferrier rearrangement

About: Ferrier rearrangement is a(n) research topic. Over the lifetime, 321 publication(s) have been published within this topic receiving 5524 citation(s).

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Journal ArticleDOI
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

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185 citations


Journal ArticleDOI
Abstract: Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides. The α-anomers predominate (ca. 90%), and the method can be used to prepare the known crystalline ethyl α-glucoside easily and in greatly improved yield. Other alkyl glycosides have been prepared similarly, and the procedure has afforded means of obtaining the cholesteryl analogue and the disaccharide derivative 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. Tri-O-acetyl-D-glucal again gave the 2,3-unsaturated glycosides on treatment with acetals in the presence of boron trifluoride; no evidence was obtained for the formation of branched-chain products produced by additions to the double bond.

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175 citations


Journal ArticleDOI
TL;DR: A highly convergent, stereocontrolled total synthesis of the potent antiproliferative agent (+)-phorboxazole A (1) has been achieved.

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Abstract: A highly convergent, stereocontrolled total synthesis of the potent antiproliferative agent (+)-phorboxazole A (1) has been achieved. Highlights of the synthesis include: modified Petasis−Ferrier rearrangements for assembly of both the C(11−15) and C(22−26) cis-tetrahydropyran rings; extension of the Julia olefination to the synthesis of enol ethers; the design, synthesis, and application of a novel bifunctional oxazole linchpin; and Stille coupling of a C(28) trimethyl stannane with a C(29) oxazole triflate. The longest linear sequence leading to (+)-phorboxazole A (1) was 27 steps, with an overall yield of 3%.

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170 citations


Book ChapterDOI
18 Dec 2001-ChemInform
Abstract: Glycals (or usually their O-substituted derivatives) are readily converted into 2,3-unsaturated glycosyl compounds with O-, C-, N-, S- or otherwise linked substituents at the anomeric position. These products have been found to be useful for a range of synthetic purposes. In particular, the C-glycosidic compounds have served as readily available starting materials for the preparation of useful non-carbohydrate compounds. While these allylic rearrangement processes are usually conducted under the influence of Lewis acid catalysts, adaptations that involve activation of the allylic substituents of the starting glycals as leaving groups under neutral conditions have been developed. General features of the reactions are described as well as applications in synthesis and extensions of the basic processes.

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141 citations


Journal ArticleDOI
Masahiro Terada1, Yasunori Toda1Institutions (1)
TL;DR: Highly anti- and enantioselective synthesis of beta-amino aldehydes having an aliphatic substituent at the beta-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis-Ferrier rearrangement.

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Abstract: Highly anti- and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis−Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.

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114 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20216
20204
20196
20184
20175
201616

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Topic's top 5 most impactful authors

Peiran Chen

11 papers, 80 citations

Jianbo Zhang

10 papers, 92 citations

Renato Dalpozzo

5 papers, 83 citations

Henok H. Kinfe

5 papers, 55 citations

Amos B. Smith

5 papers, 84 citations