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Keywords:

  • Asymmetric catalysis;
  • Organo­catalysis;
  • Michael addition;
  • Hydrogen bonds;
  • Transition states

Abstract

A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole-derived organocatalyst. Computational and NMR studies support the hydrogen-bonding activation role of the catalyst and the origin of the stereoselectivity of the process.