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

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

Tetrahedron ◽  
2007 ◽  
Vol 63 (32) ◽  
pp. 7532-7537 ◽  
Author(s):  
Abel Ros ◽  
Antonio Magriz ◽  
Hansjörg Dietrich ◽  
José M. Lassaletta ◽  
Rosario Fernández

2010 ◽  
Vol 21 (11-12) ◽  
pp. 1436-1446 ◽  
Author(s):  
Sébastien Prévost ◽  
Sébastien Gauthier ◽  
Maria Cristina Caño de Andrade ◽  
Céline Mordant ◽  
Ali Rhida Touati ◽  
...  

Synthesis ◽  
2021 ◽  
Author(s):  
Jie Jia ◽  
Fangdong Hu ◽  
Ying Xia

Transition-metal-catalyzed nucleophilic dearomatization of electron-deficient heteroarenes, such as pyridines, quinolines, isoquinolines and nitroindoles, has become a powerful method for the access of unsaturated heterocycles in recent decades. This short review summarizes nucleophilic dearomatization of electron-deficient heteroarenes with carbon- and heteroatom-based nucleophiles via transition-metal catalysis. A great number of functionalized heterocycles were obtained in this transformation. Importantly, many of these reactions were carried out in an enantioselective manner by means of asymmetric catalysis, providing a unique method for the construction of enantioenriched heterocycles. 1 Introduction 2 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes via alkynylation 3 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes via arylation 4 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes with other nucleophiles 5 Transition-metal-catalyzed nucleophilic dearomatization with nucleophiles formed in situ 6 Conclusion and outlook


Synthesis ◽  
2016 ◽  
Vol 48 (16) ◽  
pp. 2523-2539 ◽  
Author(s):  
Phannarath Phansavath ◽  
Virginie Ratovelomanana-Vidal ◽  
Pierre-Georges Echeverria ◽  
Tahar Ayad

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 353-364 ◽  
Author(s):  
Lorena De Luca ◽  
Antonio Mezzetti

The catalytic strategies developed so far for the synthesis of enantiomerically pure benzoins are reviewed. Particular attention is given to their substrate scope and limitations. Finally, this short review highlights the advantages of more atom-economic methods that have been reported recently.1 Introduction2 Benzoin Condensation2.1 Nucleophilic Carbenes as Catalysts2.2 Homocondensation of Aromatic Aldehydes2.3 Cross-Benzoin Condensation2.4 Acyloin Condensation2.5 Biocatalytic Methods3 Organocatalytic Friedel–Crafts Reaction4 Oxidative Methods4.1 α-Hydroxylation of Ketones4.2 Ketohydroxylation of Alkenes4.3 Enantiospecific Oxidation of meso-Hydrobenzoins4.4 Kinetic Resolution of Racemic Hydrobenzoins4.5 Biocatalytic Dynamic Kinetic Resolution5 Asymmetric Hemireduction of Benzils5.1 Biocatalytic Reductions – A Brief Summary5.2 Piers Hydrosilylation of Benzils5.3 Photoreduction of Benzils to Benzoins5.4 Metal-Catalyzed Hemihydrogenation of Benzils6 Conclusion and Future Challenges


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