ChemInform Abstract: ASYMMETRIC HYDROGENATION OF PROCHIRAL KETONES BY HOMOGENEOUS AND HETEROGENEOUS RHODIUM-CHIRAL DIPHOSPHINE CATALYTIC SYSTEMS

1983 ◽  
Vol 14 (29) ◽  
Author(s):  
K. YOSHINAGA ◽  
T. KITO ◽  
K. OHKUBO
Keyword(s):  
Asymmetric Hydrogenation ◽  
Catalytic Systems ◽  
Prochiral Ketones

Metal–ligand bifunctional catalysis for asymmetric hydrogenation

2005 ◽  
Vol 363 (1829) ◽  
pp. 901-912 ◽  
Author(s):  
Ryoji Noyori ◽  
Christian A Sandoval ◽  
Kilian Muñiz ◽  
Takeshi Ohkuma
Keyword(s):  
Asymmetric Catalysis ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Molecular Surface ◽  
Metal Alkoxide ◽  
Bifunctional Catalysis ◽  
Bifunctional Mechanism ◽  
Prochiral Ketones ◽  
Membered Transition State ◽  
Metal Ligand

Chiral diphosphine/1,2-diamine–Ru(II) complexes catalyse the rapid, productive and enantioselective hydrogenation of simple ketones. The carbonyl-selective hydrogenation takes place via a non-classical metal–ligand bifunctional mechanism. The reduction of the C=O function occurs in the outer coordination sphere of an 18e trans -RuH 2 (diphosphine)(diamine) complex without interaction between the unsaturated moiety and the metallic centre. The Ru atom donates a hydride and the NH 2 ligand delivers a proton through a pericyclic six-membered transition state, directly giving an alcoholic product without metal alkoxide formation. The enantiofaces of prochiral ketones are differentiated on the chiral molecular surface of the saturated RuH 2 species. This asymmetric catalysis manifests the significance of ‘kinetic’ supramolecular chemistry.

scholarly journals Crucial aspects in the design of chirally modified noble metal catalysts for asymmetric hydrogenation of activated ketones

2015 ◽  
Vol 44 (21) ◽  
pp. 7449-7464 ◽  
Author(s):  
Alfons Baiker
Keyword(s):  
Noble Metal ◽  
Noble Metals ◽  
Asymmetric Hydrogenation ◽  
Metal Catalysts ◽  
Catalytic Systems ◽  
Noble Metal Catalysts ◽  
Heterogeneous Catalytic

This tutorial review analyzes the crucial aspects, which have to be considered in the development of heterogeneous catalytic systems based on chirally modified noble metals for asymmetric hydrogenation of activated ketones.

Asymmetric hydrogenation of olefins on chiral cobalt catalytic systems

1982 ◽  
Vol 31 (9) ◽  
pp. 1847-1851 ◽  
Author(s):  
L. O. Nindakova ◽  
V. A. Pavlov ◽  
F. K. Shmidt ◽  
E. I. Klabunovskii
Keyword(s):  
Asymmetric Hydrogenation ◽  
Catalytic Systems

scholarly journals Asymmetric Hydrogenation of 1-aryl substituted-3,4-Dihydroisoquinolines with Iridium Catalysts Bearing Different Phosphorus-Based Ligands

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 914
Author(s):  
Giorgio Facchetti ◽  
Michael S. Christodoulou ◽  
Eleonora Binda ◽  
Marco Fusè ◽  
Isabella Rimoldi
Keyword(s):  
Asymmetric Hydrogenation ◽  
Catalytic Performance ◽  
Phosphine Ligand ◽  
Iridium Complexes ◽  
Complete Conversion ◽  
Catalytic Systems ◽  
Iridium Catalysts ◽  
Substituted 1

Starting from the chiral 5,6,7,8-tetrahydroquinolin-8-ol core, a series of amino-phosphorus-based ligands was realized. The so-obtained amino-phosphine ligand (L1), amino-phosphinite (L2) and amino-phosphite (L3) were evaluated in iridium complexes together with the heterobiaryl diphosphines tetraMe-BITIOP (L4), Diophep (L5) and L6 and L7 ligands, characterized by mixed chirality. Their catalytic performance in the asymmetric hydrogenation (AH) of the model substrate 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline 1a led us to identify Ir-L4 and Ir-L5 catalysts as the most effective. The application of these catalytic systems to a library of differently substituted 1-aryl-3,4-dihydroisoquinolines afforded the corresponding products with variable enantioselective levels. The 4-nitrophenyl derivative 3b was obtained in a complete conversion and with an excellent 94% e.e. using Ir-L4, and a good 76% e.e. was achieved in the reduction of 2-nitrophenyl derivative 6a using Ir-L5.

Recent Developments in Transition-Metal-Catalyzed Asymmetric Hydrogenation of Enamides

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 193-214
Author(s):  
Phannarath Phansavath ◽  
Virginie Ratovelomanana-Vidal ◽  
Sudipta Ponra ◽  
Bernard Boudet
Keyword(s):  
Academic Research ◽  
Asymmetric Hydrogenation ◽  
Nickel Catalysts ◽  
Industrial Applications ◽  
Ruthenium Catalysts ◽  
Cobalt Catalysts ◽  
Rhodium Catalysts ◽  
Catalytic Systems ◽  
Iridium Catalysts ◽  
Metal Catalyzed

AbstractThe catalytic asymmetric hydrogenation of prochiral olefins is one of the most widely studied and utilized transformations in asymmetric synthesis. This straightforward, atom economical, inherently direct and sustainable strategy induces chirality in a broad range of substrates and is widely relevant for both industrial applications and academic research. In addition, the asymmetric hydrogenation of enamides has been widely used for the synthesis of chiral amines and their derivatives. In this review, we summarize the recent work in this field, focusing on the development of new catalytic systems and on the extension of these asymmetric reductions to new classes of enamides.1 Introduction2 Asymmetric Hydrogenation of Trisubstituted Enamides2.1 Ruthenium Catalysts2.2 Rhodium Catalysts2.3 Iridium Catalysts2.4 Nickel Catalysts2.5 Cobalt Catalysts3 Asymmetric Hydrogenation of Tetrasubstituted Enamides3.1 Ruthenium Catalysts3.2 Rhodium Catalysts3.3 Nickel Catalysts4 Asymmetric Hydrogenation of Terminal Enamides4.1 Rhodium Catalysts4.2 Cobalt Catalysts5 Rhodium-Catalyzed Asymmetric Hydrogenation of Miscellaneous Enamides6 Conclusions

Recent Progress and Applications of Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 30-50
Author(s):  
Phannarath Phansavath ◽  
Virginie Ratovelomanana-Vidal ◽  
Ricardo Molina Betancourt ◽  
Pierre-Georges Echeverria ◽  
Tahar Ayad
Keyword(s):  
Transition Metal ◽  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Asymmetric Hydrogenation ◽  
Short Review ◽  
Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Catalytic Systems ◽  
Keto Esters ◽  
Metal Catalyzed

AbstractBased on the ever-increasing demand for enantiomerically pure compounds, the development of efficient, atom-economical, and sustainable methods to produce chiral alcohols and amines is a major concern. Homogeneous asymmetric catalysis with transition-metal complexes including asymmetric hydrogenation (AH) and transfer hydrogenation (ATH) of ketones and imines through dynamic kinetic resolution (DKR) allowing the construction of up to three stereogenic centers is the main focus of the present short review, emphasizing the development of new catalytic systems combined to new classes of substrates and their applications as well.1 Introduction2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution2.1 α-Substituted Ketones2.2 α-Substituted β-Keto Esters and Amides2.3 α-Substituted Esters2.4 Imine Derivatives3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution3.1 α-Substituted Ketones3.2 α-Substituted β-Keto Esters, Amides, and Sulfonamides3.3 α,β-Disubstituted Cyclic Ketones3.4 β-Substituted Ketones3.5 Imine Derivatives4. Conclusion

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