Iridium-Catalyzed Enantioselective Allylic Substitutions with Aliphatic Nitro Compounds as Prenucleophiles

Enantioselective Ir-catalyzed allylic alkylations with nitroalkanes and ethyl nitroacetate as nucleophiles are reported. Up to 99% ee was achieved using catalysts prepared by in situ activation of mixtures of phosphorus amidites and [Ir(COD)Cl]2. The method was applied to a synthesis of the antidepressant (1S,2R)-trans-2phenylcyclopentanamine.