Download PDF
Synlett 1999; 1999(S1): 867-868
DOI: 10.1055/s-1999-3106
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Iridium Ferrocenyl Diphosphine Catalyzed Enantioselective Reductive Alkylation of a Hindered Aniline

Hans-Ulrich Blaser* , Hans-Peter Buser, Hans-Peter Jalett, Benoit Pugin, Felix Spindler
  • *Novartis Services AG; E-mail: hans-ulrich.blaser@sn.novartis.com
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints 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

      >