1298116-76-3

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 24641-29-0 2-(3-methoxyphenyl)quinoline 
• 552-89-6 2-nitro-benzaldehyde 
• 358656-63-0 C₁₆H₁₃NO₄ 
• 1204482-07-4 (E)-3-(2-aminophenyl)-1-(3-methoxyphenyl)prop-2-en-1-one 
• 612-62-4 2-Chloroquinoline 
• 10365-98-7 3-methoxyphenylboronic acid 
• 1198359-70-4 2-(3-methoxyphenyl)quinoline hydrobromide 

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.

Visible-Light Induction/Br?nsted Acid Catalysis in Relay for the Enantioselective Synthesis of Tetrahydroquinolines

An efficient method merging Br?nsted acid catalysis with visible-light induction for the highly enantioselective synthesis of tetrahydroquinolines has been developed. This mild process directly transforms 2-aminoenones into 2-substituted tetrahydroquinolines with excellent enantioselectivities through a relay visible-light-induced cyclization/chiral phosphoric acid-catalyzed transfer hydrogenation reaction.

Spiro-Bicyclic Bisborane Catalysts for Metal-Free Chemoselective and Enantioselective Hydrogenation of Quinolines

A new series of spiro-bicyclic bisborane catalysts has been prepared by means of hydroboration reactions of C2-symmetric spiro-bicyclic dienes with HB(C6F5)2 and HB(p-C6F4H)2. When used for hydrogenation of quinolines, these catalysts give excellent yields and enantiomeric excesses, and show turnover numbers of up to 460. The most attractive feature of these metal-free hydrogenation reactions was the broad functional-group tolerance, making this method complementary to existing methods for quinoline hydrogenation.

Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

A chiral Bronsted acid catalyzed dehydrogenative kinetic resolution of tetrahydroquinoline derivatives, which are representative of cyclic secondary amines, based on their hydrogen transfer to aromatic imines was efficiently achieved with high enantioselectivities. This hydrogen transfer of tetrahydroquinolines to imines was not driven by their aromatization to quinolines. This dehydrogenative kinetic resolution could be also applied to the asymmetric synthesis of various benzofused heterocycles containing secondary amine cores.

Highly enantioselective spinol-derived phosphoric acid catalyzed transfer hydrogenation of diverse C=N-containing heterocycles

A highly efficient and enantioselective hydrogenation of diversely substituted C=N-containing heterocyclic compounds such as 3-aryl-1,4-benzoxazines and 2-arylquinolines was experimentally explored by using 1,1′-spirobiindane-7,7′-diol-derived chiral phosphoric acids as the catalyst. This method provides straightforward access to the corresponding tetrahydroquinolines and dihydro-2H-1,4-benzothiazines in high yields (85-99%) with excellent enantioselectivities (91-99%). The attractive features of this procedure, which include mild reaction conditions, operational simplicity, relatively low catalyst loading (1 mol-%), and high levels of enantioselectivities, make it a useful approach for the practical synthesis of optically active nitrogen-containing aromatic heterocycles.

A microporous binol-derived phosphoric acid

No slow down: A microporous recyclable heterogeneous catalyst made from a 1,1'-binaphthalene-2,2'-diol (binol)-derived phosphoric acid chloride is as active as the corresponding homogeneous catalyst when using the same mass of both in different reactions. Reaction rates, yields, and enantioselectivities are comparable. Copyright

Highly enantioselective transfer hydrogenation of quinolines catalyzed by gold phosphates: Achiral ligand tuning and chiral-anion control of stereoselectivity

A little gold goes a long way: As little as 0.01 mol % of chiral gold phosphate is sufficient to afford the asymmetric transfer hydrogenation of quinolines with high stereoselectivity (up to 98 % ee). The achiral ligands on gold were found to have conside

Highly enantioselective transfer hydrogenation of quinolines catalyzed by gold phosphates: Achiral ligand tuning and chiral-anion control of stereoselectivity

A little gold goes a long way: As little as 0.01 mol % of chiral gold phosphate is sufficient to afford the asymmetric transfer hydrogenation of quinolines with high stereoselectivity (up to 98 % ee). The achiral ligands on gold were found to have conside