Screening of a library of hemisalen ligands in asymmetric H-transfer: Reduction of aromatic ketones in water
Boukachabia, M; Vriamont, N; Lambin, D; Riant, O; Aribi-Zouioueche, L
| HERO ID | 2905792 |
|---|---|
| In Press | No |
| Year | 2014 |
| Title | Screening of a library of hemisalen ligands in asymmetric H-transfer: Reduction of aromatic ketones in water |
| Authors | Boukachabia, M; Vriamont, N; Lambin, D; Riant, O; Aribi-Zouioueche, L |
| Journal | Academie des Sciences. Comptes Rendus. Chimie |
| Volume | 17 |
| Issue | 5 |
| Page Numbers | 403-412 |
| Abstract | A library of chiral hemisalen ligands (30) was realized. The ligands were synthesized by the condensation of salicylaldehyde derivatives with amino-alcohols (amino-indanol or substituted amino-ethanol) and characterized. These ligands associated with ruthenium (II) precursors were tested on the asymmetric transfer hydrogenation (ATH) of aromatic ketones by sodium formate in water. The different substituent pattern on the ligand (electronic and hindrance effects on different positions) as well as the ruthenium precursor were investigated. The best compromise in terms of conversion and chiral induction led to the complex [RuCl2(mesitylene)](2) coordinated to (1S,2R)-1-((E)-(3(dimethyl(phenyl)silyl)-2-hydroxy-5-methoxy benzylidene) amino)-2,3-dihydro-1H-inden-2-ol (L25). It reduces acetophenone in 95% yield and 91% ee in 18 h at 30 degrees C. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved. |
| Doi | 10.1016/j.crci.2013.08.011 |
| Wosid | WOS:000335290700001 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Asymmetric catalysis; Hydride transfer; Hemisalen ligands; Ruthenium; Aromatic ketones |