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Mechanistic Complexity of Asymmetric Transfer Hydrogenation with Simple Mn-Diamine Catalysts.
van Putten, Robbert; Filonenko, Georgy A; Gonzalez de Castro, Angela; Liu, Chong; Weber, Manuela; Müller, Christian; Lefort, Laurent; Pidko, Evgeny.
Afiliación
  • van Putten R; Inorganic Systems Engineering Group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology, Van der Maasweg 9, 2629 HZ, Delft, The Netherlands.
  • Filonenko GA; Inorganic Systems Engineering Group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology, Van der Maasweg 9, 2629 HZ, Delft, The Netherlands.
  • Gonzalez de Castro A; InnoSyn B.V, Urmonderbaan 22, 6167 RD, Geleen, The Netherlands.
  • Liu C; Inorganic Systems Engineering Group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology, Van der Maasweg 9, 2629 HZ, Delft, The Netherlands.
  • Weber M; Freie Universität Berlin, Institute of Chemistry and Biochemistry, Fabeckstrasse 34/36, D-14195 Berlin, Germany.
  • Müller C; Freie Universität Berlin, Institute of Chemistry and Biochemistry, Fabeckstrasse 34/36, D-14195 Berlin, Germany.
  • Lefort L; InnoSyn B.V, Urmonderbaan 22, 6167 RD, Geleen, The Netherlands.
  • Pidko E; Inorganic Systems Engineering Group, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology, Van der Maasweg 9, 2629 HZ, Delft, The Netherlands.
Organometallics ; 38(16): 3187-3196, 2019 Aug 26.
Article en En | MEDLINE | ID: mdl-31474784
The catalytic asymmetric transfer hydrogenation (ATH) of ketones is a powerful methodology for the practical and efficient installation of chiral centers. Herein, we describe the synthesis, characterization, and catalytic application of a series of manganese complexes bearing simple chiral diamine ligands. We performed an extensive experimental and computational mechanistic study and present the first detailed experimental kinetic study of Mn-catalyzed ATH. We demonstrate that conventional mechanistic approaches toward catalyst optimization fail and how apparently different precatalysts lead to identical intermediates and thus catalytic performance. Ultimately, the Mn-N,N complexes under study enable quantitative ATH of acetophenones to the corresponding chiral alcohols with 75-87% ee.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Organometallics Año: 2019 Tipo del documento: Article País de afiliación: Países Bajos Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Organometallics Año: 2019 Tipo del documento: Article País de afiliación: Países Bajos Pais de publicación: Estados Unidos