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Synlett 2001; 2001(1): 0147-0149
DOI: 10.1055/s-2001-9713
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A Straightforward Route to E-γ-Aryl-α-oxobutenoic Esters by One-step Acid-catalysed Crotonisation of Pyruvates

Gilles Dujardin* , Stéphane Leconte, Alexandre Bénard, Eric Brown
  • *UMR 6011 CNRS-Université du Maine, Laboratoire de Synthèse Organique (UCO2M), Faculté des Sciences, Avenue Olivier Messiaen, F-72085 Le Mans Cedex 9, France; E-mail: dujardin@univ-lemans.fr
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Publication Date:
31 December 2001 (online)

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A new and highly simple method for the synthesis of E-γ-aryl-α-oxobutenoic esters is described. This unprecedented one-step procedure is based on an unexpected nucleophilic reactivity of alkyl pyruvates towards aromatic aldehydes in refluxing dichloromethane, when using catalytic amounts of Cu(OTf)2 and in the presence of stoichiometric amounts of trimethyl orthoformate in the case of electron-rich aldehydes. Under these conditions, yields obtained are uniformly higher than those obtained by previous multistep procedures.

benzylidenepyruvate - crotonisation - copper (II) triflate - trimethyl orthoformate - heterodiene