Reaction of unsaturated phosphonate monoesters with bromo- and iodo(bis-collidine) hexafluorophosphates

André, Virginie; Lahrache, Hind; Robin, Sylvie; Rousseau, G.

doi:10.1016/j.tet.2007.07.032

Cited by 42 publications

(27 citation statements)

References 28 publications

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“…Bromo‐ and iodo‐(bis‐collidine)‐hexafluorophosphates have been shown to convert alkene phosphonate monoesters 12 (Scheme ) into their cyclized five‐, six‐, and seven‐membered products 13 at room temperature (r.t.) with 1.3 equiv. of reagent 15. The reaction most likely proceeds by halo coordination with the double bond, followed by exo intramolecular attack by the OH.…”

Section: Intramolecular Nucleophilic‐addition‐type Reactionsmentioning

confidence: 99%

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

et al. 2014

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The cover picture shows the mechanism of DNAzyme displacement required to control DNAzyme catalysis for the implementation of programmable molecular logic, as reported by D. Stefanovic, S. W. Graves et al. on . This approach combines the advantages of DNA strand displacement for programming reaction pathways with the inherent catalytic activity of DNAzymes for amplified fluorescent readout. Arbitrary input strand detection was achieved through the rational introduction of mismatched bases. Given the range of chemical reactions catalyzed by DNAzymes, this work offers a powerful mechanism for controlling a range of covalent chemical modifications by using DNA strand displacement. The image was produced with assistance from Kim Miller.

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Section: Intramolecular Nucleophilic‐addition‐type Reactionsmentioning

confidence: 99%

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

et al. 2014

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“…Known alcohol 10a, which was prepared from l-(+)-DET according to reported procedures, [9] was converted into 7a in four steps. Known alcohol 10a, which was prepared from l-(+)-DET according to reported procedures, [9] was converted into 7a in four steps.…”

Section: Scheme 1 Retrosynthetic Analysis Of Stereoisomers 2a-dmentioning

confidence: 99%

“…Known alcohol 10a, which was prepared from l-(+)-DET according to reported procedures, [9] was converted into 7a in four steps. The key step was a tandem ring-closing/ cross-metathesis reaction in which lactone formation and fragment coupling were accomplished in one pot.…”

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Tandem Ring‐Closing/Cross‐Metathesis Approach for the Synthesis of Synargentolide B and Its Stereoisomers

2013

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The stereoselective syntheses of synargentolide B and its three stereoisomers have been accomplished from L‐(+)‐ and D‐(–)‐diethyl tartrates, D‐ribose, and D‐mannitol as chiral pool starting materials. The key step was a tandem ring‐closing/cross‐metathesis reaction in which lactone formation and fragment coupling were accomplished in one pot. The spectroscopic data of synthetic product 2c were in agreement with those reported for the natural product. Synargentolide B isolated by Rivett et al. and the compound isolated by Pereda‐Miranda et al. are not diastereomers, but rather they are identical.

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“…Among them, aryl‐substituted allylphosphonates are useful starting materials for the preparation of dienes and polyenes via the Horner–Wadsworth–Emmons–Wittig reaction . These aryl‐substituted allylphosphonates are obtained by the reaction of substituted cinnamyl halides or alcohols with trialkyl phosphites; however, most of the corresponding halides and alcohols have to be prepared via multistep syntheses. Wittig reagents and vinylphosphonates have also been applied to react with aldehydes, giving aryl‐substituted allylphosphonates …”

Section: Introductionmentioning

confidence: 99%

Mizoroki–Heck Reaction of Aryl Halides and Dialkyl Allylphosphonates in Water Catalyzed by Reusable Palladium Nanoparticles

et al. 2015

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Commercial [PdCl 2 (NH 3 ) 2 ]w as appliedt oc atalyze the Mizoroki-Heck coupling of aryl halides with dialkyl allylphosphonates using iPr 2 NH as the base in water under aerobic conditions. The reactionw as conducted at8 08C( for aryl iodides) or 120 8C( for aryl bromides) for 36 h, giving the correspondinga ryl-substituted allylphosphonates in good to excellent yields, and both water-soluble and insoluble aryl halidesc ould be utilized in this reaction. After extracting the reaction solution with ethyl acetate, the residual aqueous solution was reused for the same reaction several times, and the true catalystwas found to be palladium nanoparticles. In addition, ao ne-pot synthesis of 1,4-diarylbuta-1,3-dienes, which combinedt his catalytic reactionw ith the Horner-Wadsworth-Emmons-Wittig reaction, was also performed. Results and DiscussionAt the outset, iodobenzene (1a)a nd diethyl allylphosphonate (2a)w eres elected as representativer eactants for optimization of the reactionc onditions (Table 1). When [PdCl 2 (NH 3 ) 2 ]a ssociated with aw ater-soluble cationic 2,2'-bipyridyl ligand [43] [a] W.

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Reaction of unsaturated phosphonate monoesters with bromo- and iodo(bis-collidine) hexafluorophosphates

Cited by 42 publications

References 28 publications

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

Tandem Ring‐Closing/Cross‐Metathesis Approach for the Synthesis of Synargentolide B and Its Stereoisomers

Mizoroki–Heck Reaction of Aryl Halides and Dialkyl Allylphosphonates in Water Catalyzed by Reusable Palladium Nanoparticles

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