Selective Reduction of Carbonyl Compounds via (Asymmetric) Transfer Hydrogenation on Heterogeneous Catalysts

Synthesis ◽  
2020 ◽  
Vol 52 (04) ◽  
pp. 504-520 ◽  
Author(s):  
Eszter Baráth

Based on the ever-increasing demand for optically pure compounds, the development of efficient methods to produce such products is very important. Homogeneous asymmetric catalysis occupies a prominent position in the ranking of chemical transformations, with transition metals coordinated to chiral ligands being applied extensively for this purpose. However, heterogeneous catalysts have the ability to further extend the field of asymmetric transformations, because of their beneficial properties such as high stability, ease of separation and regeneration, and the possibility to apply them in continuous processes. The main challenge is to find potential synthetic routes that can provide a chemically and thermally stable heterogeneous catalyst having the necessary chiral information, whilst keeping the catalytic activity and enantioselectivity equally high (or even higher) than the corresponding homogeneous counterpart. Within this short review, the most relevant immobilization modes and preparative strategies depending on the support material used are summarized. From the reaction scope viewpoint, metal catalysts supported on the various solid materials studied in (asymmetric) transfer hydrogenation of carbonyl compounds are selected and represent the main focus of the second part of this overview.1 Introduction2 Synthesis of Chiral Heterogeneous Catalysts2.1 Immobilization of Homogeneous Asymmetric Catalysts2.1.1 Immobilization on Inorganic Supports2.1.2 Immobilization on Organic Polymers as Supports2.1.3 Immobilization on Dendrimer-Type Materials as Supports2.1.4 Self-Supported Chiral Catalysts: Coordination Polymers2.1.5 Immobilization Using Non-Conventional Media2.2 Chirally Modified Metal Surfaces for Heterogeneous Asymmetric Catalysis3 Examples of Transfer Hydrogenation on Heterogeneous Catalysts3.1 Silicon-Immobilized Catalysts3.2 Carbon-Material-Immobilized Catalysts3.3 Polymer-Immobilized Catalysts3.4 Magnetic-Nanoparticle-Immobilized Catalysts4 Conclusions

2016 ◽  
Vol 420 ◽  
pp. 149-158 ◽  
Author(s):  
Lidiya O. Nindakova ◽  
Nataliya M. Badyrova ◽  
Vladimir V. Smirnov ◽  
Sergey S. Kolesnikov

RSC Advances ◽  
2016 ◽  
Vol 6 (39) ◽  
pp. 33126-33131 ◽  
Author(s):  
Yuan-Zhao Mo ◽  
Hui-Fang Nie ◽  
Yang Lei ◽  
Dong-Xu Zhang ◽  
Xiao-Ye Li ◽  
...  

Six ferrocene-based chiral ligands were prepared and applied in ATH reaction of multiple-carbonyl compounds as RuCl(p-cymene)[Ts-DPEN] did.


2017 ◽  
Vol 57 (1) ◽  
Author(s):  
Gabriela Huelgas ◽  
Haydee Rojas Cabrera ◽  
Domingo Madrigal ◽  
Ratnasamy Somanathan ◽  
Pilar Guzmán ◽  
...  

New chiral monosulfonamides <strong>…</strong>6-16 containing (11<em>R</em>,12<em>R</em>)-diamino-9,10-dihydro-9,10-ethanoanthracene as carbon skeleton were prepared. Compounds <strong>6-12</strong>, <strong>15</strong> and <strong>16</strong> were used as optically active ligands in the enantioselective ethylation of benzaldehyde. Moreover, the monosulfonamides <strong>6-10</strong> were tested in the asymmetric transfer hydrogenation (ATH) of acetophenone with Rh(Cp*)L* complex.


1987 ◽  
Vol 327 (1) ◽  
pp. C15-C17 ◽  
Author(s):  
Serafino Gladiali ◽  
Giorgio Chelucci ◽  
Giovanna Chessa ◽  
Giovanna Delogu ◽  
Franco Soccolini

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