Skip to Main content Skip to Navigation
Journal articles

ENANTIOSELECTIVE REDUCTION OF PROCHIRAL KETONES PROMOTED BY AMINO AMIDE RUTHENIUM COMPLEXES: A DFT STUDY

Abstract : The origin of enantioselectivity in the reaction of chiral Ru amino amide complexes in the asymmetric transfer hydrogenation of acetophenone was investigated using DFT calculations. For the most stable active catalysts, the full free energy profiles for the reaction were calculated according to the concerted hydrogen transfer mechanism. We succeeded in reproducing the experimentally observed enantioselectivity for the studied Ru amino amide complexes. Our results indicate that the high enantioselectivity can be explained by a stabilizing CH-π interaction existing between the phenyl group of acetophenone and the aromatic substituent of the catalyst, which plays a significant role in selectivity. Finally, our results show that important insights can be obtained with such a theoretical approach not simply to explain the origin of the reaction asymmetry but also to predict the enantiomeric excess. This can help experimentalists to design new enantioselective catalysts.
Document type :
Journal articles
Complete list of metadata

https://hal.archives-ouvertes.fr/hal-03374397
Contributor : Carine Michel Connect in order to contact the contributor
Submitted on : Tuesday, October 12, 2021 - 9:59:45 AM
Last modification on : Tuesday, January 4, 2022 - 6:21:31 AM
Long-term archiving on: : Thursday, January 13, 2022 - 6:42:16 PM

File

ArticleYazid2020_v13_unmarked....
Files produced by the author(s)

Identifiers

Citation

Y Meftah, Y Boumedjane, Paul Fleurat-Lessard, F Delbecq, Carine Michel. ENANTIOSELECTIVE REDUCTION OF PROCHIRAL KETONES PROMOTED BY AMINO AMIDE RUTHENIUM COMPLEXES: A DFT STUDY. Journal of Organometallic Chemistry, Elsevier, 2021, ⟨10.1016/j.jorganchem.2021.121765⟩. ⟨hal-03374397⟩

Share

Metrics

Les métriques sont temporairement indisponibles