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Keywords:

  • allylic compounds;
  • asymmetric synthesis;
  • homogeneous catalysis;
  • organocatalysis;
  • synthetic methods
Thumbnail image of graphical abstract

Double agent: The title reaction using the guanidine catalyst 1 can deliver both enantiomers of the product with excellent enantioselectivity by judicious choice of the double bond geometry of the the β,γ-unsaturated carbonyl compound. Computational studies reveal the possible origin of the inversed enantioselectivity, and the potential for enantiodivergent synthesis chiral amine-containing substrates is attractive.