Synthesis, resolution and structure of axially chiral atropisomeric N-arylimides

Reported is the synthesis and structures of a new series of axially chiral molecules based on restricted rotation. The ortho-substituted N-arylimides have enantiomeric atropisomers that are stable and separable at room temperature. The compounds are notable for their ease of synthesis as well as positioning of functionality (a carboxylic acid and an amine) in a highly asymmetric configuration.