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Keywords:

  • asymmetric catalysis;
  • alkylation;
  • deracemization;
  • diastereodivergence;
  • pi-allyl isomerization;
  • reaction mechanisms

Abstract

Dynamic deracemizations are robust strategies wherein a racemate is converted into a single enantiopure product in 100 % yield. A process can be defined as diastereodivergent if multiple diastereomers of the product are possible and if a specific process offers the ability to generate each and every one of them by fine-tuning the reaction conditions. Palladium-catalyzed asymmetric allylic alkylation with stabilized nucleophiles is a versatile strategy that can be used to achieve this goal. In this concept, we summarize the advances that have been made in this field. We also introduce and develop the novel concepts of diastereodivergent deracemization and diastereodivergent de-epimerization.