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Keywords:

  • aldol reaction;
  • carbon–carbon bond cleavage;
  • organocatalysis;
  • reaction mechanisms;
  • trifluoroacetate release
Thumbnail image of graphical abstract

An organocatalytic asymmetric direct aldol addition reaction that involves cleavage of a carbon–carbon bond through the release of trifluoroacetate was developed. The protocol is wide in scope, generating the desired oxindoles of biological interest in nearly quantitative yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee) and diastereoselectivities (up to 99:1 d.r.).