scholarly journals Vancomycin-Iridium (III) Interaction: An Unexplored Route for Enantioselective Imine Reduction

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2771
Author(s):  
Giorgio Facchetti ◽  
Sara Pellegrino ◽  
Raffaella Bucci ◽  
Donatella Nava ◽  
Raffaella Gandolfi ◽  
...  
Keyword(s):  
Catalytic System ◽  
Coordination Sphere ◽  
Hybrid System ◽  
Asymmetric Reduction ◽  
Analytical Techniques ◽  
Transfer Hydrogenation ◽  
Chiral Structure ◽  
Hybrid Catalysts ◽  
Saturation Kinetics ◽  
Imine Reduction

The chiral structure of antibiotic vancomycin (Van) was exploited as an innovative coordination sphere for the preparation of an IrCp* based hybrid catalysts. We found that Van is able to coordinate iridium (Ir(III)) and the complexation was demonstrated by several analytical techniques such as MALDI-TOF, UV, Circular dichroism (CD), Raman IR, and NMR. The hybrid system so obtained was employed in the Asymmetric Transfer Hydrogenation (ATH) of cyclic imines allowing to obtain a valuable 61% e.e. (R) in the asymmetric reduction of quinaldine 2. The catalytic system exhibited a saturation kinetics with a calculated efficiency of Kcat/KM = 0.688 h−1mM−1.

An iron–nitrogen doped carbon and CdS hybrid catalytic system for efficient CO2 photochemical reduction

2021 ◽  
Vol 57 (16) ◽  
pp. 2033-2036
Author(s):  
Jin-Han Guo ◽  
Xiao-Yao Dao ◽  
Wei-Yin Sun
Keyword(s):  
Aqueous Solution ◽  
Catalytic System ◽  
Hybrid System ◽  
Photochemical Reduction ◽  
Nitrogen Doped ◽  
Nitrogen Doped Carbon

A new iron–nitrogen doped carbon and CdS hybrid system was developed to efficiently reduce CO2 to CO under UV/vis light (AM 1.5G) irradiation in aqueous solution.

scholarly journals Bis-NHC–Ag/Pd(OAc)2 Catalytic System Catalyzed Transfer Hydrogenation Reaction

Catalysts ◽  
2020 ◽  
Vol 11 (1) ◽  
pp. 8
Author(s):  
Hui-Ju Chen ◽  
Chien-Cheng Chiu ◽  
Tsui Wang ◽  
Dong-Sheng Lee ◽  
Ta-Jung Lu
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
High Efficiency ◽  
Aqueous Media ◽  
Hydrogenation Reaction ◽  
Transfer Hydrogenation ◽  
Terminal Alkynes ◽  
Wide Range ◽  
Transfer Hydrogenation Reaction

The bis-NHC–Ag/Pd(OAc)2 catalytic system (NHC = N-heterocyclic carbene), a combination of bis-NHC–Ag complex and Pd(OAc)2, was found to be a smart catalyst in the Pd-catalyzed transfer hydrogenation of various functionalized arenes and internal/terminal alkynes. The catalytic system demonstrated high efficiency for the reduction of a wide range of various functional groups such as carbonyls, alkynes, olefins, and nitro groups in good to excellent yields and high chemoselectivity for the reduction of functional groups. In addition, the protocol was successfully exploited to stereoselectivity for the transformation of alkynes to alkenes in aqueous media under air. This methodology successfully provided an alternative useful protocol for reducing various functional groups and a simple operational protocol for transfer hydrogenation.

Ruthenium-catalyzed asymmetric reduction of 1,3-diketones using transfer hydrogenation

2001 ◽  
Vol 42 (30) ◽  
pp. 5005-5007 ◽  
Author(s):  
Janine Cossy ◽  
Florence Eustache ◽  
Peter I Dalko
Keyword(s):  
Asymmetric Reduction ◽  
Transfer Hydrogenation

scholarly journals Asymmetric transfer hydrogenation of prochiral ketones catalyzed by aminosulfonamide-ruthenium complexes in ionic liquid

2011 ◽  
Vol 9 (1) ◽  
pp. 175-179 ◽  
Author(s):  
Zhongqiang Zhou ◽  
Yong Sun ◽  
Aiqing Zhang
Keyword(s):  
Ionic Liquid ◽  
Catalytic System ◽  
Ruthenium Complexes ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Prochiral Ketones

AbstractChiral aminosulfonamides containing imidazolium group were used as ligands for the ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral ketones in ionic liquid, affording good to excellent conversions and enantiomeric excesses. The catalytic system could be easily recovered and reused several times.

Synthesis of a new class of ligands derived from isosorbide and their application to asymmetric reduction of aromatic ketones by transfer hydrogenation

2011 ◽  
Vol 35 (11) ◽  
pp. 2622 ◽  
Author(s):  
Khanh-Duy Huynh ◽  
Houssein Ibrahim ◽  
Emile Kolodziej ◽  
Martial Toffano ◽  
Giang Vo-Thanh
Keyword(s):  
Asymmetric Reduction ◽  
Transfer Hydrogenation ◽  
Aromatic Ketones ◽  
New Class

scholarly journals Highly Asymmetric Reduction of New Benzofuryl and Benzothiophenyl α-Amino Ketones

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 49
Author(s):  
Agnieszka Tafelska-Kaczmarek ◽  
Marcin Kwit ◽  
Bartosz Stasiak
Keyword(s):  
High Performance ◽  
Asymmetric Reduction ◽  
Theoretical Calculations ◽  
Transfer Hydrogenation ◽  
Central Position ◽  
Chiral Hplc ◽  
Naturally Occurring ◽  
Approved Drugs ◽  
High Yields ◽  
Derivatives Of

Heterocyclic compounds play an important role in medicinal chemistry and occupy a central position in synthetic organic chemistry. Both benzofuran and benzothiophene are considered as very important structures due to their diverse biological and pharmacological profile. Many clinically approved drugs are synthetic and naturally occurring substituted benzofuryl and benzothiophenyl derivatives in conjunction with other heterocycles. Therefore, a new series of α-amino ketone (containing various azole rings) derivatives of benzofuran and benzothiophene are synthesized and subjected to the transfer hydrogenation with formic acid, catalyzed by RhCl[(R,R)-TsDPEN](C5Me5). The corresponding optically active β-amino alcohols are obtained in high yields and excellent enantioselectivities (93%–99%), as determined by chiral HPLC (high-performance liquid chromatography). The absolute configuration of the products is confirmed by means of ECD (electronic circular dichroism) spectroscopy, supported by theoretical calculations.

scholarly journals Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: synthesis, characterization and catalytic transfer hydrogenation activity

2019 ◽  
Vol 48 (31) ◽  
pp. 11838-11847 ◽  
Author(s):  
Joseph P. Byrne ◽  
Pauline Musembi ◽  
Martin Albrecht
Keyword(s):  
Metal Complex ◽  
Hybrid System ◽  
Transfer Hydrogenation ◽  
Hydrogenation Catalyst ◽  
Catalytic Transfer Hydrogenation ◽  
Hydrogenation Activity ◽  
Catalytic Transfer

Triazolylidene NHCs decorated with a carbohydrate wingtip group were complexed to a ruthenium(ii) center. Deprotection of the carbohydrate in the metal complex affords a carbohydrate–NHC hybrid system for use as a transfer hydrogenation catalyst.

Asymmetric reduction of methoxy substituted β-tetralones using transfer hydrogenation

2004 ◽  
Vol 15 (23) ◽  
pp. 3715-3717 ◽  
Author(s):  
Muneto Mogi ◽  
Kaoru Fuji ◽  
Manabu Node
Keyword(s):  
Asymmetric Reduction ◽  
Transfer Hydrogenation

Enantioselective Catalytic Methods for the Elaboration of Chiral Tetrahydro-β-carbolines and Related Scaffolds

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2605-2620 ◽  
Author(s):  
Nicolas Glinsky-Olivier ◽  
Xavier Guinchard
Keyword(s):  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Asymmetric Hydrogenation ◽  
Transfer Hydrogenation ◽  
Chiral Molecules ◽  
Chiral Phosphoric Acid ◽  
Hydrogenation Reactions ◽  
Synthetic Intermediates ◽  
Catalyzed Reactions

Tetrahydro-β-carbolines are important synthetic intermediates in the total synthesis of natural products and of compounds exhibiting strong bioactivities. Over the last decades, catalytic methods using chiral catalysts have been described for their synthesis. This review covers catalytic and enantioselective methods to access chiral tetrahydro-β-carbolines and their applications in the elaboration of complex chiral molecules.1 Introduction2 Asymmetric Reduction of Dihydro-β-carbolines2.1 Asymmetric Transfer Hydrogenation Reactions2.2 Asymmetric Hydrogenation Reactions2.3 Biocatalyzed Reduction of Dihydro-β-carbolines3 Organocatalyzed Pictet–Spengler Reactions3.1 Chiral Thiourea-Catalyzed Reactions3.2 Chiral Phosphoric Acid Catalyzed Reactions4 Pictet–Spengler Reactions of In Situ Generated Cyclic Iminiums5 Organocatalyzed Functionalization of Dihydro-β-carboliniums6 Organocatalyzed Alkylation of Tetrahydro-β-carbolines7 Biocatalyzed Dynamic Kinetic Resolution of Tetrahydro-β-carbolines8 Conclusion and Perspectives

Asymmetric transfer hydrogenation reactions of N-sulfonylimines by using alcohols as hydrogen sources

2018 ◽  
Vol 54 (39) ◽  
pp. 4963-4966 ◽  
Author(s):  
Fan Yang ◽  
Jingchao Chen ◽  
Guoli Shen ◽  
Xuexin Zhang ◽  
Baomin Fan
Keyword(s):  
Catalytic System ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Hydrogenation Reactions

A palladium/zinc co-catalytic system was established and successfully utilized in the asymmetric transfer hydrogenation reactions of N-sulfonylimines with alcohols as hydrogen sources.

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