Asymmetric Synthesis of Axially Chiral Compound Utilizing Planar Chiral Transition Metal Complexes and Their Development for Dynamic Complexes

Axially chiral biaryls and N-aryl indoles are stereoselectively prepared by utilizing planar chiral transition metal complexes. Both enantiomers of axial biaryls and N-aryl indoles could be synthesized starting from an identical enantiomerically pure arene chromium complex. We applied this method to the synthesis of vancomycin A-B ring system and korupensamines. Kinetically controlled biaryl and N-aryl indole transition metal complexes with sp(3) heteroatom at the side chain could be converted to thermodynamically stable complexes involving the inversion or transfer of planar chirality. These results indicate that transition metal fragment in planar chiral eta(6)-transition metal complexes can be utilized as dynamic complexes with mobile chiral auxiliary.