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Keywords:

  • Allylation;
  • Enantioselectivity;
  • Ion pairs;
  • Lithium;
  • Homogeneous catalysis

Abstract

In an enolate Claisen rearrangement, deprotonated allyl phenylacetate undergoes a smooth conversion at –78 °C to 2-phenyl-4-pentenoic acid under palladium(0) catalysis. By using labelled starting materials in crossover experiments, the reaction is shown to follow a dissoziative, non-concerted, non-[3,3]-sigmatropic mechanism that involves palladium complexes and carboxylic-acid dianions as intermediates.