The ease of separation, simple regeneration, and the usually high stability of solid catalysts facilitating continuous production processes have stimulated the development of heterogeneous asymmetric hydrogenation catalysis. The simplest and so far most promising strategy to induce enantioselectivity to solid metal catalysts is their modification by chiral organic compounds, as most prominently represented by the cinchona-modified Pt and Pd catalysts for the asymmetric hydrogenation of activated C═O and C═C bonds. In this Review, we provide a systematic account of the research accomplished in the past decade on noble metal-based heterogeneous asymmetric hydrogenation of prochiral C═O and C═C bonds, including all important facets of these catalytic systems. The advances made are critically analyzed, and future research challenges are identified.
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http://dx.doi.org/10.1021/acs.chemrev.7b00272 | DOI Listing |
J Am Chem Soc
January 2025
Faculty of Pharmaceutical Sciences, Shenzhen University of Advanced Technology, Shenzhen 518107, China.
The synthesis of chiral tetrahydroquinolines (THQs) has garnered significant interest from medicinal chemists due to their frequent presence as pharmacophores in bioactive compounds. While existing synthetic methods have primarily focused on THQs with single or multiple endocyclic chiral centers, the selective construction of THQs with both and cyclic chiral centers remains a significant challenge that requires further development. This study introduces a dynamic kinetic resolution (DKR)-based transfer hydrogenation of racemic 2-substituted quinolines, which yields structurally novel chiral THQs with consecutive and cyclic chiral centers in excellent yields and stereoselectivities (59 examples, with generally >20:1 dr and >90% ee, up to three consecutive stereocenters).
View Article and Find Full Text PDFOrg Lett
January 2025
Laboratory for Materials and Structures, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
Developed Co-MgO/TiO was applicable to C-N bond formation by direct amination of primary and secondary alcohols with NH via a borrowing hydrogen protocol. Selective synthesis of primary, secondary, and tertiary amines was achieved by controlling the reaction conditions. Asymmetric secondary amines can be synthesized by the coupling of alcohols and amines.
View Article and Find Full Text PDFMikrochim Acta
January 2025
Department of Chemistry, School of Science, Xihua University, Chengdu, 610039, PR China.
Based on the enhanced peroxidase-like activity of carbon dots nanozymes (CDszymes), with a specific oxidation reaction of D-amino acid oxidase catalysing the formation of HO from D-amino acid, an ultrasensitive sensing platform, was constructed for the quantitative detection of D-amino acids in saliva. With the increase of D-amino acids concentration, the blue color of catalytic product gradually deepend, the fluorescence CDszymes gradually quenched, and the temperature gradually increased. Using D-alanine as D-amino acid models, the detection limits of D-alanine in colorimetric/photothermal/fluorescent mode were 0.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Huazhong University of Science and Technology, School of Materials Science and Engineering, 1037 Luoyu Road, 430074, Wuhan, CHINA.
Organics electrooxidation coupled hydrogen production has attracted increasing attention due to the low operation voltage. Nevertheless, the spontaneous production of hydrogen coupled with organics valorization remains challenging. Herein, we develop ultrathin Au/Pt twin nanowire (NW) catalysts for both electrochemical glucose oxidation and hydrogen evolution reaction towards a spontaneous hydrogen production system.
View Article and Find Full Text PDFNano Lett
January 2025
Zhejiang Engineering Research Center for Tissue Repair Materials and Wenzhou Key Laboratory of Biomaterials and Engineering and Wenzhou Key Laboratory of Biophysics, Wenzhou Institute, University of Chinese Academy of Sciences, Wenzhou 325001, China.
Saccharides and peptides with markedly disparate stereochemical features serve as pivotal chiral molecular partners in living systems. The importance of glycosylation in influencing glycopeptide self-assembly has been recognized. However, how different chiral combinations of saccharides and peptides influence the macroscopic hydrogel mechanics, fiber nanomechanics, asymmetric molecular packing, and thermodynamic changes during glycopeptide self-assembly remains unknown.
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