Synlett

A Straightforward Route to E-γ-Aryl-α-oxobutenoic Esters by One-step Acid-catalysed Crotonisation of Pyruvates

G Dujardin, S Leconte, A Bénard, E Brown

Index: Dujardin; Leconte; Benard; Brown Synlett, 2001 , # 1 p. 147 - 149

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Citation Number: 18

Abstract

Abstract: A new and highly simple method for the synthesis of Eg-aryl-a-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. ...