608525-30-0

Upstream product

• 17507-24-3 2-(2-quinolyl)propane 
• 166329-43-7 N-tert-butoxycarbonyl-2-bromomethylaniline 
• 53627-32-0 2-isopropyl-1,2,3,4-tetrahydroquinoline 
• 5344-90-1 2-Aminobenzyl alcohol 
• 598-75-4 3-methyl-2-butanol 
• 62-53-3 aniline 
• 1775-44-6 (2E)-4-methylpent-2-enoic acid 

Downstream Products

• 17507-24-3 2-(2-quinolyl)propane 

Relevant academic research and scientific papers

Manganese-Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π–π Interaction**

The non-noble metal-catalyzed asymmetric hydrogenation of N-heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asymmetric hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97 % ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which is competitive with the activity of most effective noble metal catalysts for this reaction. The precise regulation of the enantioselectivity were ensured by a π–π interaction.

Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3Pincer Catalyst

A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.

A Synthetic Route to Chiral Benzo-Fused N-Heterocycles via Sequential Intramolecular Hydroamination and Asymmetric Hydrogenation of Anilino-Alkynes

An efficient sequential intramolecular hydroamination/asymmetric hydrogenation reaction under catalysis of a single chiral ruthenium complex or a binary system consisting of achiral gold complex and chiral ruthenium complex has been reported. A diverse range of enantioenriched benzo-fused N-heterocycles, including 1,2,3,4-tetrahydroquinoline, indoline, and 2,3,4,5-tetrahydro-1H-benzo[b]azepine derivatives, were obtained from anilino-alkynes in high yields (up to 98%) with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. This protocol features good functional group tolerance and high atom economy. Furthermore, this catalytic protocol is applicable to gram-scale synthesis of a naturally occurring alkaloid, (-)-Angustureine.

P -Chiral, N -phosphoryl sulfonamide Br?nsted acids with an intramolecular hydrogen bond interaction that modulates organocatalysis

Br?nsted acids exemplified by OttoPhosa I (5c) were designed and evaluated in the asymmetric transfer hydrogenation of quinolines. Their catalytic properties are modulated by an intramolecular hydrogen bond that rigidifies their catalytic cavity, accelerates the reaction rate and improves enantioselectivity.

Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid

A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.

Strong Br?nsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh-thiourea chiral phosphine complex: Via anion binding

Rhodium catalyzed asymmetric hydrogenation of both isoquinolines and quinolines provides a new method to synthesize chiral tetrahydroisoquinolines and tetrahydroquinolines. By introducing strong Br?nsted acid HCl, anion binding between the substrate and t

Bio-mediated oxidative resolution of racemic 2-substituted 1,2,3,4-tetrahydroquinolines

Whole cell of Pseudomonas monteilii ZMU-T01 strains mediated oxidative resolution of racemic 2-substituted 1,2,3,4-tetrahydroquinolines has been successfully described. A series of highly enantioselective 2-substituted 1,2,3,4-tetrahydroquinoline derivatives were obtained in up to 50% conversion and >99% ee.

Efficient enantioselective hydrogenation of quinolines catalyzed by conjugated microporous polymers with embedded chiral BINAP ligand

Chiral Ir complexes were successfully used in the asymmetric hydrogenation of olefins, ketones, and quinolines. However, almost all the catalytic systems could not tolerate a high catalyst loading because of the formation of an irreversible iridium dimer and trimer during the reaction. It is expected that higher catalytic activity may be achieved if the Ir-complexes were isolated in space. The development of conjugated microporous polymers (CMPs) gives the opportunity for the spatial separation of the complexes. A series of chiral CMPs based on the chiral (R)-BINAP ligand (BINAP-CMPs) with different surface areas were synthesized. The BINAP ligands were separately distributed in the framework and were three times more active than the homogeneous catalyst (TOF 340 h-1 VS 100 h-1) for the asymmetric hydrogenation of quinolines.

Thiourea as an efficient organocatalyst for the transfer hydrogenation of 2-substituted quinoline derivatives

This study reports on the first transfer hydrogenation of 2-substituted quinolines promoted by a thiourea catalyst with Hantzsch ester as the hydrogen source. A wide range of quinoline derivatives, including 2-alkylquinolines and 2-arylquinolines, were ef

The remarkable effect of a simple ion: Iodide-promoted transfer hydrogenation of heteroaromatics

I can do it! Accelerated by simple iodide ions, rhodium-catalysed transfer hydrogenation can be readily performed on quinolines, isoquinolines and quinoxalines, affording the tetrahydro products in high yields with low catalyst loading (see scheme). Copyright