856703-36-1

Upstream product

• 1613-43-0 2-cyclohexylquinoline 
• 5344-90-1 2-Aminobenzyl alcohol 
• 823-76-7 Cyclohexyl methyl ketone 
• 123629-22-1 (RS)-2-cyclohexyl-1,2,3,4-tetrahydroquinoline 
• 166329-43-7 N-tert-butoxycarbonyl-2-bromomethylaniline 

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.

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.

Enantioselective Synthesis of Tetrahydroquinolines by Borrowing Hydrogen Methodology: Cooperative Catalysis by an Achiral Iridacycle and a Chiral Phosphoric Acid

We report herein the highly enantioselective synthesis of 2-substituted tetrahydroquinolines through borrowing hydrogen, a process recognized for its environmentally benign and atom-economical nature. The use of an achiral iridacycle complex in combination with a chiral phosphoric acid as catalysts was the key to the development of this highly efficient and enantioselective transformation.

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.

Development of chiral phosphoric acids based on ferrocene-bridged paracyclophane frameworks

This work deals with the development of a new family of planar chiral phosphoric acids based on a ferrocenophane/paracyclophane scaffold. The synthetic approach has been improved by taking advantage of a chiral phosphorylating agent to access enantiomerically enriched acids via diastereomers separation. These phosphoric acids have been used as catalysts for the enantioselective H-transfer reduction of α-substituted quinolines with Hantzsch esters. Optimization of both the catalyst and the Hantzsch reductant allowed ee values in the range 82-92% to be attained starting from α-arylquinolines. Copyright

Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst

The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl]2 in THF resulted in a highly efficient catalyst system for asymmetric hydrogenation of quinolines at quite low catalyst loadings (0.05-0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h-1) and productivities (TON up to 43000). The same catalyst was also successfully applied to the asymmetric hydrogenation of trisubstituted pyridines with nearly quantitative yields and up to 98% ee. In these two reactions, the addition of I2 additive is indispensable; but the amount of I2 has a different effect on catalytic performance. The Royal Society of Chemistry 2010.