Iridium-Catalyzed Asymmetric Ring Opening of Azabicyclic Alkenes by Amines

The enantioselective ring-opening reactions of azabicyclic alkenes with primary and secondary aromatic amine nucleophiles are reported using an iridium catalyst generated in situ from 1.5 mol % of [Ir(COD)Cl]2 and 3 mol % of (S)-BINAP. The reaction affords the corresponding trans-1,2-diamine derivatives in moderate to good yields with moderate to high enantioselectivities (up to 97% ee). The trans-configuration of the 1,2-diamino product 2g was confirmed by X-ray crystallography.