Development of <i>C</i>₂-Symmetric Chiral Bifunctional Triamines: Synthesis and Application in Asymmetric Organocatalysis

Abstract

The synthesis and application of a newly designed C₂-symmetric chiral bifunctional triamine family ( C₂-CBT) is reported. These enantiopure chiral triamine scaffolds can be accessed in multigram amounts from simple amino acids while avoiding chromatographic purification. As a proof of principle, C₂-CBT has been studied in the aldol reaction of cyclic ketones with isatins, with the target tertiary alcohols being formed in a highly efficient manner. Catalyst recovery by simple extraction techniques and subsequent reuse has been performed.