Showing papers on "Claisen rearrangement published in 1987"
163 citations
TL;DR: Etude de l'effet d'un substituant alcoxy sur le groupe allyl d'(allyl vinyl) ethers sur la vitesse de transposition Claisen de ces ethers as mentioned in this paper.
Abstract: Etude de l'effet d'un substituant alcoxy sur le groupe allyl d'(allyl vinyl) ethers sur la vitesse de transposition Claisen de ces ethers
148 citations
TL;DR: The C-glycosyl compounds produced by mono-Claisen rearrangement were suitable for Pd(0)-catalyzed allylic alkylations, providing an unusually facile entry into the pseudomonic acid-ring systems.
75 citations
69 citations
TL;DR: Transposition de Claisen a partir de O-methyl et O-benzyl glycolates d'alcene-2yle is described in this article, where a synthese de trimethyl-3,7,11 dodecanol-1 et de dimethyl 3,7 pentadecanol-2
Abstract: Transposition de Claisen a partir de O-methyl et O-benzyl glycolates d'alcene-2yle. Application a la synthese de trimethyl-3,7,11 dodecanol-1 et de dimethyl-3,7 pentadecanol-2
61 citations
55 citations
46 citations
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43 citations
TL;DR: In this paper, the Claisen rearrangements with the enol ethers of cyclic ketones are shown to proceed with a high level of either anti or syn diastereoselection, respectively.
40 citations
TL;DR: The Claisen rearrangement has been widely used in the synthesis of natural heterocyclic products as discussed by the authors, and there are now several alkaloid syntheses in which the Claisen re-arrangement features as a key step.
Abstract: Publisher Summary The Claisen rearrangement of heteroaromatic allyl ethers shows many similarities to the rearrangement of simple benzenoid aromatic allyl ethers. Mechanistically, the reactions are for the most part genuine [3,3]-sigmatropic rearrangements, although the presence of nitrogen in the aromatic ring does allow alternative pathways to operate, and hence more than one product may be formed. However, these alternative products are usually easily rationalized on mechanistic grounds. One other difference between the Claisen rearrangement of heteroaromatic ally1 ethers (or thioethers) and their benzene counterparts is that the rearrangement product is often more stable in the one form than as the hydroxy (or mercapto) heteroaromatic compound. The Claisen rearrangement has been widely used in the synthesis of natural heterocyclic products. Although much of this work has been in the coumarin series, there are now several alkaloid syntheses in which the Claisen rearrangement features as a key step. Indications are that the Claisen rearrangement continues to hold an important role in organic chemistry.
TL;DR: In this paper, an enantiospecific synthesis of α-kainic acid from L-aspartic acid was achieved in which the C-3 to C-4 bond was formed by a stereocontrolled enolate Claisen rearrangement.
Abstract: An enantiospecific synthesis of (–)-α-kainic acid (1) from L-aspartic acid (7) has been achieved in which the C-3 to C-4 bond is formed by a stereocontrolled enolate Claisen rearrangement [(13)→(14)] which delivers the correct geometry at the C-3 and C-4 asymmetric centres.
TL;DR: Pseudomonic acid C (V) is synthesized from the hydroxycyclopentenylacetate (I) via the key intermediates (II) - (IV) as discussed by the authors.
Abstract: Pseudomonic acid C (V) is synthesized from the hydroxycyclopentenylacetate (I) via the key intermediates (II) - (IV).
TL;DR: Synthetic confirmation of the C(1′)-(S)-configuration of (+)-dihydropallescensin-2 (1) is reported, the key reaction being a chiron-mediated asymmetric aza-Claisen rearrangement (6→7) as mentioned in this paper.
TL;DR: In this paper, a general approach to dolastane diterpenes from (R)-(+)-limonene is described, and the total synthesis of the title compounds is described.
TL;DR: In this paper, the authors describe the successful construction of a significant portion of the gelsemine structure using the use of the mixed acetal radical cyclization and a sequential transannular alkylation -Claisen rearrangement sequence.
TL;DR: The authors derives de dimethoxy-15,16 erythrinane a partir de la photocyclisation du perchlorate de dihydro-3,4dimethoxy 6,7 ethoxycarbonylmethyl-2 (=R-2) trimethylsilylmethyl 4, pentene 4,4 yl-1 isoquinoleinium en dimethiox-6,7' R-2' tetrahydro-1',2,3,3',4,4,5,4' methylene-3
Abstract: Synthese de derives de dimethoxy-15,16 erythrinane a partir de la photocyclisation du perchlorate de dihydro-3,4 dimethoxy-6,7 ethoxycarbonylmethyl-2 (=R-2) trimethylsilylmethyl-4' pentene-4' yl-1 isoquinoleinium en dimethoxy-6',7' R-2' tetrahydro-1',2',3',4' methylene-3 spiro [cyclohexane-1:1'-isoquinoleine]
TL;DR: In this paper, a method for preparing hindered cycloalkanone ketals in very pure form is presented, as well as a useful modification for synthesizing the required 2-cyclohexenols from alkyl anisoles with a minimum number of undesired side products.
TL;DR: In this article, the treatment of stereodefined ω-halo-2-iodoalkene derivatives, prepared via stereoselective addition reactions of alkynes, with either n −BuLi (1 equiv) or t -BuLi(2 equiv).
TL;DR: In this paper, the dioxanone-to-dihydropyran Claisen rearrangement has been used for the efficient conversion of (S)-(−)-ethyl lactate to the erythronolide A and B C(7)C(13) subunits 19, 23, and 27 via the common synthetic intermediates 13 and 22.
TL;DR: Synthese de la methoxy-1 methoxyethoxymethoxy-4 methyl-7 perhydro dicyclopenta [a,d] cyclooctenone-8 a partir de l'octahydro epoxy- 1,6 azulenecarboxylate-4 de t-butyle
Abstract: Synthese de la methoxy-1 methoxyethoxymethoxy-4 methyl-7 perhydro dicyclopenta [a,d] cyclooctenone-8 a partir de l'octahydro epoxy-1,6 azulenecarboxylate-4 de t-butyle
TL;DR: In this paper, le compose de depart est l'[allyloxy-5' hydroxy-2' phenyl]-1 [methyl-2 dithiolanne-1,3yl-2]-5 pentadiene-2,4one-1
Abstract: Le compose de depart est l'[allyloxy-5' hydroxy-2' phenyl]-1 [methyl-2 dithiolanne-1,3yl-2]-5 pentadiene-2,4one-1
TL;DR: Claisen rearrangement of methyl-3-aryloxy-2-(aryloxymethyl)prop-2-enoates (4) in refluxing N,N-diethylaniline gave 3-(2-hydroxyphenylmethylene) -3,4-dihydro-2H-1-benzopyran-2.1.
TL;DR: In this article, 8,14-Cedranoxide has been synthesized starting from 3,4-dimethoxyphenol, wherein 6-acetoxymethyl-2,6-dimethyl-9-methoxytricyclo[53101,5]undec-9en-8,11-dione as a key intermediate has been produced efficiently by means of electrochemical methods.
TL;DR: In this paper, the authors demonstrate that the stereochemical outcome of this type of rearrangements may be controlled by the spatial requirements of substituents external to the pericyclic array.