Iridium Ferrocenyl Diphosphine Catalyzed Enantioselective Reductive Alkylation of a Hindered Aniline

All articles of this category The enantioselective reductive alkylation of 2-methyl-5-ethyl-aniline (MEA) with methoxyacetone - using a catalyst generated in situ from [Ir(cod)Cl] 2 and ( R )-( S )-PPF-P(3,5-xyl) 2 - to give enriched ( S )- N -(2-ethyl-6-methylphenyl)- N -(1′-methoxymethyl)-ethyl-amine is described. At 80 bar and 50 °C in the presence of iodide and methane sulfonic acid and with cyclohexane as solvent, complete conversion is reached within 14 h with a substrate to catalyst ratio of 10'000 and an ee of 76-78%. The effect of solvent and acid type were found to be important. To our knowledge, this is the first enantioselective reductive alkylation ever reported. enantioselective reductive alkylation - hindered N-alkyl aniline - Ir-ferrocenyl diphosphine - acid catalysis - ( S )-metolachlor