Metal-Free SN2′ Decarboxylative Rearrangement of β-Keto Esters (pages 4170–4175)
Vincent Bizet, Valérie Lefebvre, Jérôme Baudoux, Marie-Claire Lasne, Agathe Boulangé, Stéphane Leleu, Xavier Franck and Jacques Rouden
Article first published online: 1 JUN 2011 | DOI: 10.1002/ejoc.201100120
Allyl acetoacetates bearing an electron-withdrawing group on the double bondundergo a tandem SN2′–decarboxylation–SN2′ reaction in the presence of a nucleophilic tertiary amine or triphenylphosphane. Yields were particularly satisfactory from α-substituted acetoacetates. It was shown that the reaction was intermolecular and was induced by a nucleophile and not by a base.