Stereoselective synthesis of axially chiral N-C bonds in N-aryl indoles

N-Aryl indoles with axially chiral N-C bonds were synthesized by stereoselective nucleophilic aromatic substitution reactions of planar chiral arene chromium complexes. Stereoselective chromium tricarbonyl migration was achieved in the sterically hindered N-aryl indole chromium complex by refluxing in toluene.