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7931065 
Journal Article 
Iridium ferrocenyl diphosphine catalyzed enantioselective reductive alkylation of a hindered aniline 
Blaser, HU; Buser, HP; Jalett, HP; Pugin, B; Spindler, F 
1999 
1 
Synlett
ISSN: 0936-5214
EISSN: 1437-2096 
SPEC. ISS. 
867-868 
English 
WOS:000081569000009 
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