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Keywords:

  • Aldol reactions;
  • Asymmetric catalysis;
  • Enantioselectivity;
  • Organocatalysis;
  • Water chemistry

Abstract

C2-Symmetric (S)-prolinamides modified with ionic groups and bearing achiral diamine units were synthesized. Their potency as reusable organocatalysts for asymmetric aldol reactions of cycloalkanones or methyl ketones with aromatic (heteroaromatic) aldehydes in the presence of water was demonstrated. The 1,4-diaminobenzene-derived catalyst exhibited good catalytic performance and excellent recoverability over at least 15 reaction–regeneration cycles under the studied conditions.