Jump to main content
Jump to site search

Issue 16, 2016
Previous Article Next Article

The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts

Author affiliations

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 article 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. 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.

Graphical abstract: The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts

Back to tab navigation

Publication details

The article was received on 03 Feb 2016, accepted on 09 Mar 2016 and first published on 21 Mar 2016


Article type: Perspective
DOI: 10.1039/C6DT00476H
Citation: Dalton Trans., 2016,45, 6756-6781
  •   Request permissions

    The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts

    P. A. Dub and J. C. Gordon, Dalton Trans., 2016, 45, 6756
    DOI: 10.1039/C6DT00476H

Search articles by author

Spotlight

Advertisements