Recent advances in fluorinated vinylstannanes and their synthetic utility

Shen, Yanchang

doi:10.1016/j.jorganchem.2005.11.011

Cited by 6 publications

(3 citation statements)

References 53 publications

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“…1,2 Stannyldesulfonylation of the vinyl sulfone 2a followed by halodestannylation of the resulting vinyl stannanes 2b was a key step in the synthesis of 5′-deoxy-5′-(halomethylene)adenosines 2c , which were found to be potent inhibitors of S- adenosyl-L-homocysteine (AdoHcy) hydrolase and valuable probes to study hydrolytic activity of the enzyme 3–5. Stannyldesulfonylation/protiodestannylation of the (α-fluoro)vinyl sulfones and stannyldesulfonylation/halodestannylation of the vinyl sulfones procedures allowed synthesis of the various 5′-deoxy-5′-(halomethylene)nucleoside analogues derived from uridine,6 L-adenosine,7 3′-deoxyadenosine,8 and 6- N- cyclopropyladenosine9 as well as 5′-deoxy-5′-(halomethylene)ribose derivatives,10 among others 11. The vinyl sulfone precursors have been conveniently prepared by treatment of the nucleoside 2′-keto or 5′-aldehyde derivatives with the sulfonyl-stabilized Wittig reagents,1,12,13 and chemistry of the vinyl-sulfone modified carbohydrates and nucleosides has been reviewed 14.…”

Section: Introductionmentioning

confidence: 99%

Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

Wnuk

Sacasa

Restrepo

2009

Nucleosides, Nucleotides & Nucleic Acids

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Treatment of the protected (E)-5′-deoxy-5′- [(p-toluenesulfonyl)methylene]uridine and adenosine derivatives with tributyl-or triphenylgermane hydride (AIBN/toluene/Δ) effected radical-mediated germyldesulfonylations to give 5′-(tributyl-or triphenylgermyl)methylene-5′-deoxyuridine and adenosine derivatives as single (E)-isomers. Analogous treatment of 2′-deoxy-2′-[(phenylsulfonyl) methylene]uridine with Ph 3 GeH afforded the corresponding vinyl triphenylgermane product. Stereoselective halodegermylation of the (E)-5′-(tributylgermyl)methylene-5′-deoxy nucleosides with N-iodosuccinimide or N-bromosuccinimide provided the Wittig-type (E)-5′-deoxy-5′-(halomethylene) nucleosides quantitatively, while no halodegermylations was observed with the 5′-deoxy-5′-(triphenylgermyl)methylene counterparts. Treatment of the vinyl trialkylgermanes with aqueous trifluoroacetic acid effected protiodegermylation, while vinyl triarylgermanes were stable under the acidic conditions.

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Section: Introductionmentioning

confidence: 99%

Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

Wnuk

Sacasa

Restrepo

2009

Nucleosides, Nucleotides & Nucleic Acids

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“…Interestingly, when the reactions of benzyl halides were carefully examined, formation of fluorovinyl sulfones was observed indicating that a second elimination step occurred after the initial substitution reaction. Vinyl fluorides can be prepared from electrophilic fluorination of vinyllithiums , or stannanes , via the Horner−Wadsworth−Emmons condensation of α-fluorophosphonates with carbonyls, − desulfonylation, , stannyldesulfonylation, − silyl and germyldesulfonylation , of fluorovinyl sulfones, as well as Peterson and Julia olefination. Fluorovinyl sulfones, precursors of vinyl fluorides, are commonly synthesized using the Horner−Wittig reaction.…”

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confidence: 99%

Efficient Nucleophilic Fluoromethylation and Subsequent Transformation of Alkyl and Benzyl Halides Using Fluorobis(phenylsulfonyl)methane

et al. 2009

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An efficient methodology for the nucleophilic fluoromethylation of alkyl and benzyl halides using alpha-fluoro-alpha-(phenylsulfonyl)methane (1) as a highly versatile reagent is reported. Using benzyl halides, stereospecific one-pot synthesis of alpha-fluorovinyl compounds such as alpha-fluorostyrylsulfones, alpha-fluorocinnamates, and alpha-fluorochalcones has been achieved. The methodology has been extended toward the synthesis of alpha-substituted fluoroalkane derivatives using selective reductive desulfonylation conditions.

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“…The recent article reported by Shen [93] reviewed the chemistry of fluorinated vinylstannanes and their use in medicinal and agricultural chemistry for the synthesis of fluorine containing biologically active compounds.…”

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confidence: 99%

Recent Progress in the Chemistry of Allenes

Hassan

2007

COS

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Allenes are important compounds in organic and synthetic organic chemistry and therefore a large number of studies on their synthesis and reactions have been reported so far. We report the most recent methods for the synthesis of allenes, including optically active forms and fluorinated and gem-difluorinated allenes, in this paper. Reactions such as nucleophilic addition of allenes were classified and discussed in details according to the nature of the nucleophile either oxygen, nitrogen, carbon or sulfur, whereas, inter-and intra-molecular cycloadditions reactions with a variety of unsaturated functionality were separately discussed. A collection of some useful reactions such as coupling reactions of allenes mediated by organometallic reagents, intramolecular cyclization of allenes with tethered amines, asymmetric dihydroxylation, and epoxidation of allenes are also included.

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Recent advances in fluorinated vinylstannanes and their synthetic utility

Cited by 6 publications

References 53 publications

Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

Efficient Nucleophilic Fluoromethylation and Subsequent Transformation of Alkyl and Benzyl Halides Using Fluorobis(phenylsulfonyl)methane

Recent Progress in the Chemistry of Allenes

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