Synthesis of (e)-vinylic tellurides and their transformation into α,β-unsaturated esters and carboxylic acids

Dabdoub, Miguel J.; Begnini, Mauro L.; Cassol, Tânia M.; Guerrero, Palimécio G.; Silveira, Cláudio C.

doi:10.1016/0040-4039(95)01585-6

Cited by 34 publications

(6 citation statements)

References 17 publications

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“…Two groups have independently reported the zirconium−tellurium exchange reaction for the preparation of E -vinylic tellurides . The reaction is performed by the treatment of an alkyne with Schwartz's reagent, Cp 2 Zr(H)Cl, where the vinyl zirconocene chloride 92 intermediate undergoes an exchange reaction with butyltellurenyl halide to exclusively give E -vinylic tellurides 93 in high yields (Scheme ).…”

Section: 23 Preparation Of Vinylic Tellurides By a Metal−tellurium Ex...mentioning

confidence: 99%

Vinylic Tellurides: From Preparation to Their Applicability in Organic Synthesis

et al. 2006

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Section: 23 Preparation Of Vinylic Tellurides By a Metal−tellurium Ex...mentioning

confidence: 99%

Vinylic Tellurides: From Preparation to Their Applicability in Organic Synthesis

et al. 2006

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“…13 The protocol has been successfully applied to the preparations of organophosphorus, 14 -selenium 15 and -tellurium compounds, 16 and amines. 17 Surprisingly this strategy has not been adapted previously for the synthesis of sulfones.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, it has become very popular that syn-addition of Schwartz's reagent onto a terminal alkyne followed by treatment with electrophiles provides a trans-functionalized alkene with a high level of stereochemical purity. 13 The protocol has been successfully applied to the preparations of organophosphorus, 14 -selenium 15 and -tellurium compounds, 16 and amines. 17 Surprisingly this strategy has not been adapted previously for the synthesis of sulfones.…”

Section: Methodsmentioning

confidence: 99%

A Facile Regio- and Stereocontrolled Synthesis of (E)-Disubstituted Vinyl Sulfones via Transformation of Alkenylzirconocenes with Sulfonyl Chlorides

Duan

Huang

1999

Synlett

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Alkenylzirconium reagents, readily obtained by hydrozirconation of terminal alkynes, can smoothly react with sulfonyl chlorides to afford (E)-disubstituted vinyl sulfones in moderate to good yields. Some g-functionalized vinyl sulfones can be also conveniently synthesized.Vinyl sulfones have served as a class of compounds of proven value in organic synthesis due to the reactivity offered by the sulfonyl functional group. 1 Thus vinyl sulfones are excellent acceptors for Michael additions 2 and 2π partners in cycloaddition reactions. 3 In addition, alkylative desulfonylation has also provided a new strategy for stereospecific alkene synthesis. 4 Recently, γ-functionalized vinyl sulfones have been occasionally applied to rearrangement reactions and cyclization reactions, 5 which has considerably extended the utilities of vinyl sulfones in organic synthesis.The aforementioned methodology relies strongly upon regio-and stereoselective construction of the precursor vinyl sulfones, and numerous strategies have been developed toward this goal. A broadly used strategy involved the process of addition prior to elimination to alkenes. Typical examples could include iodosulfonylation / dehydroiodination, 6 sulfonomercuriation/demercuriation, 7 selenosulfonylation/oxidation/elimination reaction. 8 While these procedures can efficiently provide vinyl sulfones, the number of the linear steps involved by the strategy is unfavorable to the overall yield, and the toxicity of selenium and mercury is also unfriendly to the environment. Alternative convergent process involved the combination of a sulfone-stabilized carbanion with a carbonyl compound. In this regard, Knoevenagel condensation 9 and Horner-Wittig reaction 10 achieved great successes and the (E)-vinyl sulfone was the exclusive product, but the preparation of the starting materials such as sulfonomethylphosphonates could be both inconvenient and timeconsuming. In addition, protodesilylation of α-phenylsulfonyl allyl silanes also provided an indirect approach to vinyl sulfones. 11 To our knowledge, no well-established method is used to prepare γ-functionalized vinyl sulfones. 12 Herein, we hope to report a facile regio-and stereocontrolled synthesis of (E)-disubstituted vinyl sulfones by the conversion of alkenylzirconocenes with sulfonyl chlorides. With the strategy, not only general vinyl sulfones but also γ-functionalized vinyl sulfones can be conveniently prepared in moderate to good yields (Scheme and Table). SchemeRecently, it has become very popular that syn-addition of Schwartz's reagent onto a terminal alkyne followed by treatment with electrophiles provides a trans-functionalized alkene with a high level of stereochemical purity. 13 Downloaded by: Queen's University. Copyrighted material.

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“…Complementary to hydrotelluration producing (Z)-vinyl tellurides, the hydrometalation (with DIBAL-H 44 or Schwartz reagent 45 ) of terminal alkynes followed by their reaction with an electrophilic tellurium reagent allows the stereoselective preparation of the corresponding (E)-vinyl tellurides 42 (Scheme 13).…”

Section: Cross-coupling Reactions Based On Organotelluridesmentioning

confidence: 99%

The Use of Butyl Organotellurides in the Synthesis of Natural Bioactive Compounds

Wendler¹,

Santos²

2009

Synlett

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Synthesis of (e)-vinylic tellurides and their transformation into α,β-unsaturated esters and carboxylic acids

Cited by 34 publications

References 17 publications

Vinylic Tellurides: From Preparation to Their Applicability in Organic Synthesis

Vinylic Tellurides: From Preparation to Their Applicability in Organic Synthesis

A Facile Regio- and Stereocontrolled Synthesis of (E)-Disubstituted Vinyl Sulfones via Transformation of Alkenylzirconocenes with Sulfonyl Chlorides

The Use of Butyl Organotellurides in the Synthesis of Natural Bioactive Compounds

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