1190876-74-4

Upstream product

• 323-91-1 2-(4-fluoro-phenyl)-quinoline 
• 552-89-6 2-nitro-benzaldehyde 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 3792-93-6 C₁₅H₁₀FNO₃ 
• 194979-77-6 tert-butyl 2-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 1435944-11-8 tert-butyl (2-(3-(4-fluorophenyl)-3-oxopropyl)phenyl)carbamate 
• 2005-43-8 2-bromoquinoline 
• 1765-93-1 4-fluoroboronic acid 
• 612-62-4 2-Chloroquinoline 
• 1402568-43-7 (±)-2-(4-fluorophenyl)-1,2,3,4-tetrahydroquinoline 
• 5344-90-1 2-Aminobenzyl alcohol 

Relevant academic research and scientific papers

Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-Catalyzed Asymmetric Hydrogenation: Solvent-Dependent Enantioselective Control and Mechanistic Investigations

Ir-catalyzed asymmetric hydrogenation of quinolines was developed, and both enantiomers of chiral tetrahydroquinoline derivatives could be easily obtained, respectively, in high yields with good enantioselectivities through the adjustment of reaction solvents (toluene/dioxane: up to 99% yield, 98% ee (R), TON = 680; EtOH: up to 99% yield, 94% ee (S), TON = 1680). It provided an efficient and simple synthetic strategy for the enantiodivergent synthesis of chiral tetrahydroquinolines, and gram-scale asymmetric hydrogenation proceeded well with low-catalyst loading in these two reaction systems. A series of deuterium-labeling experiments, control experiments, and 1H NMR and electrospray ionization-mass spectrometry experiments have been conducted, and a reasonable and possible reaction process was revealed on the basis of these useful observations.

Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?

A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.

One-pot biomimetic synthesis of chiral tetrahydroquinoline compound

The invention provides a method for one-pot biomimetic synthesis of a chiral tetrahydroquinoline compound, wherein the chiral tetrahydroquinoline compound is synthesized by starting from a simple andeasily available 2-aminochalcone substrate through one-pot biomimetic synthesis, and the enantiomeric excess of the chiral tetrahydroquinoline compound can reach 92%. The method is simple, convenientand practical to operate, high in enantioselectivity, good in yield, environmentally friendly, green and mild in reaction condition, and has potential practical application value.

Cooperative Organocatalysis: A Systematic Investigation of Covalently Linked Organophosphoric Acids for the Stereoselective Transfer Hydrogenation of Quinolines

A series of covalently linked bis- and trisphosphoric acids was investigated for their application in the stereoselective transfer-hydrogenation of quinolines. In a combined experimental and theoretical study, it was found that the number and relative pos

A one-pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines: Via asymmetric reductive amination (ARA)

Asymmetric reductive amination for the synthesis of both chiral tetrahydroquinolines (THQs) and tetrahydroisoquinolines (THIQs) has been realized with an Ir/ZhaoPhos catalytic system via a one-pot N-Boc deprotection/intramolecular asymmetric reductive amination (ARA) sequence. Control experiments reveal that HCl plays a vital role to the success of this transformation. The HCl acid assists the removal of the N-Boc protecting group and also provides chloride ions to interact with the thiourea moiety in ZhaoPhos, thus leading to excellent reaction enantiocontrol.

Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Br?nsted Acid

Interlocked molecules, such as catenanes, rotaxanes, and molecular knots, have become interesting candidates for the development of sophisticated chemical catalysts. Herein, we report the first application of a catenane-based catalyst in asymmetric organo

Enantioselective Reduction of 3-Substituted Quinolines with a Cyclopentadiene-Based Chiral Br?nsted Acid

Enantioselective reduction of 3-substituted quinolines has been achieved using a cyclopentadiene-based chiral Bronsted acid as catalyst and Hantzsch ester as hydrogen donor, affording the corresponding tetrahydroquinolines in good enantioselectivities.

Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation

The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic Ruthenium catalysts: Scope, mechanism, and origin of enantioselectivity

Asymmetric hydrogenation of quinolines catalyzed by chiral cationic η6-arene-N-tosylethylenediamine-Ru(II) complexes have been investigated. A wide range of quinoline derivatives, including 2-alkylquinolines, 2-arylquinolines, and 2-functionalized and 2,3-disubstituted quinoline derivatives, were efficiently hydrogenated to give 1,2,3,4-tetrahydroquinolines with up to >99% ee and full conversions. This catalytic protocol is applicable to the gram-scale synthesis of some biologically active tetrahydroquinolines, such as (-)-angustureine, and 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, a key intermediate for the preparation of the antibacterial agent (S)-flumequine. The catalytic pathway of this reaction has been investigated in detail using a combination of stoichiometric reaction, intermediate characterization, and isotope labeling patterns. The evidence obtained from these experiments revealed that quinoline is reduced via an ionic and cascade reaction pathway, including 1,4-hydride addition, isomerization, and 1,2-hydride addition, and hydrogen addition undergoes a stepwise H+/H- transfer process outside the coordination sphere rather than a concerted mechanism. In addition, DFT calculations indicate that the enantioselectivity originates from the CH/π attraction between the η6-arene ligand in the Ru-complex and the fused phenyl ring of dihydroquinoline via a 10-membered ring transition state with the participation of TfO- anion.