The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts
Abstract
The catalytic hydrogenation of prochiral ketones with second and third-row transition metal complexes bearing chelating chiral ligands containing at least one N–H functionality has achieved unparalleled performance, delivering, in the best cases, chiral alcohols with up to 99.9% ee using extremely small catalyst loadings (~10-5 mol%). Hence the efficacy of this reaction has closely approached that of natural enzymatic systems and the reaction itself has become one of the most efficient artificial catalytic reactions developed to date. This paper describes the current level of understanding of the mechanism of enantioselective hydrogenation and transfer hydrogenation of aromatic ketones with pioneering prototypes of bifunctional catalysts, the Noyori and Noyori–Ikariya complexes. Finally, analysis presented herein expands the concept of “metal–ligand cooperation”, redefines the term “cooperative ligand” and introduces “H–/H+ outer-sphere hydrogenation” as a novel paradigm in outer-sphere hydrogenation.
- Authors:
-
- Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
- Publication Date:
- Research Org.:
- Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1409757
- Report Number(s):
- LA-UR-16-20907
Journal ID: ISSN 1477-9226
- Grant/Contract Number:
- AC52-06NA25396
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Dalton Transactions
- Additional Journal Information:
- Journal Volume: 45; Journal Issue: 16; Journal ID: ISSN 1477-9226
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Dub, Pavel A., and Gordon, John C. The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts. United States: N. p., 2016.
Web. doi:10.1039/C6DT00476H.
Dub, Pavel A., & Gordon, John C. The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts. United States. https://doi.org/10.1039/C6DT00476H
Dub, Pavel A., and Gordon, John C. Mon .
"The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts". United States. https://doi.org/10.1039/C6DT00476H. https://www.osti.gov/servlets/purl/1409757.
@article{osti_1409757,
title = {The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts},
author = {Dub, Pavel A. and Gordon, John C.},
abstractNote = {The catalytic hydrogenation of prochiral ketones with second and third-row transition metal complexes bearing chelating chiral ligands containing at least one N–H functionality has achieved unparalleled performance, delivering, in the best cases, chiral alcohols with up to 99.9% ee using extremely small catalyst loadings (~10-5 mol%). Hence the efficacy of this reaction has closely approached that of natural enzymatic systems and the reaction itself has become one of the most efficient artificial catalytic reactions developed to date. This paper describes the current level of understanding of the mechanism of enantioselective hydrogenation and transfer hydrogenation of aromatic ketones with pioneering prototypes of bifunctional catalysts, the Noyori and Noyori–Ikariya complexes. Finally, analysis presented herein expands the concept of “metal–ligand cooperation”, redefines the term “cooperative ligand” and introduces “H–/H+ outer-sphere hydrogenation” as a novel paradigm in outer-sphere hydrogenation.},
doi = {10.1039/C6DT00476H},
journal = {Dalton Transactions},
number = 16,
volume = 45,
place = {United States},
year = {Mon Mar 21 00:00:00 EDT 2016},
month = {Mon Mar 21 00:00:00 EDT 2016}
}
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