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Carboxylate‐Directed Tandem Functionalisations of α,β‐Dihaloalkenoic Acids with 1‐Alkynes: A Straightforward Access to ( Z )‐Configured, α,β‐Substituted γ‐Alkylidenebutenolides
Author(s) -
Inack Ngi Samuel,
Cherry Khalil,
Héran Virginie,
Commeiras Laurent,
Parrain JeanLuc,
Duchêne Alain,
Abarbri Mohamed,
Thibonnet Jérôme
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102570
Subject(s) - furan , tandem , scheme (mathematics) , chemistry , computer science , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , materials science , mathematical analysis , composite material
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‐5 H ‐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‐5 H ‐furan‐2‐ones (see scheme).