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Keywords:

  • asymmetric catalysis;
  • cinchona alkaloids;
  • Michael addition;
  • organocatalysis;
  • ureas
Thumbnail image of graphical abstract

Natural not always best: Novel N-aryl urea and thiourea derivatives of dihydrocinchona alkaloids serve as efficient catalysts for the asymmetric addition of dimethyl malonate to a range of nitroalkenes. Catalytic activity and selectivity depend strongly on the relative configuration at C8/C9. Catalysts with “non-natural” inverted configuration at C9 display excellent activity and enantioselectivity at loadings as low as 0.5 mol %.