Carboxylate-Directed Tandem Functionalizations of α,β-Dihaloalkenoic Acids with 1-Alkynes: A Straightforward Access to (Z)-Configured, α,β-Substituted γ-Alkylidenebutenolides

An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactio...

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Bibliographic Details
Published inChemistry : a European journal Vol. 17; no. 49; pp. 13692 - 13696
Main Authors Inack-Ngi, Samuel, Cherry, Khalil, Héran, Virginie, Commeiras, Laurent, Parrain, Jean-Luc, Duchêne, Alain, Abarbri, Mohamed, Thibonnet, Jérôme
Format Journal Article
LanguageEnglish
Published Wiley-VCH Verlag 07.11.2011
Subjects
Chemical Sciences
Organic chemistry
copper catalysis
domino reactions
heterocycles
ring closure
butyrolactones
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Summary:An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactions, providing 3-substituted and 3,4-disubstituted 5-ylidene-5H-furan-2-ones
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201102570