An axially chiral phosphine ligand based on restricted rotation in N-arylimides

Described is the preparation, resolution, and absolute configuration of a new axially chiral monodentate phosphine ligand. The chirality of the ligand is derived from restricted rotation about a central NimideCaryl bond, resulting in enantiomeric atropisomers that are stable and separable up to >120°C. Finally, the ability of the new axially chiral phosphine ligand is demonstrated in a Pd-catalyzed allylic alkylation reaction.