608525-32-2

Upstream product

• 95279-34-8 2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline 
• 1200112-80-6 methyl (2E)-5-(3,4-dimethoxyphenyl)-2-pentenoate 
• 1200112-82-8 (2E)-5-(3,4-dimethoxyphenyl)-2-penten-1-ol 
• 6380-23-0 3,4-dimethoxystyrene 
• 1360807-88-0 (-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline 
• 1360807-86-8 (2E)-5-(3,4-dimethoxyphenyl)pent-2-en-1-yl methyl carbonate 
• 91-63-4 2-methylquinoline 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 529-37-3 4(1H)-quinolinone 
• 23308-83-0 (2-nitrobenzyl)triphenylphosphonium bromide 
• 104967-54-6 2-(3,4-dimethoxy-β-phenethyl)-1,2,3,4-tetrahydroquinoline 
• 132283-74-0 2-(3,4-dimethoxyphenyl)ethylmagnesium bromide 

Downstream Products

• 442-33-1 (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives

(Chemical Equation Presented) Enantioselective hydrogenation of quinoline derivatives catalyzed by phosphine-free chiral cationic Cp*Ir(OTf)(CF 3T8DPEN) complex (CF3TsDPEN = N-(p-trifluoromethylbenzenesulfonyl)-1,2-diphenylethylene-diamine) afforded the 1,2,3,4-tetrahydroquinoline derivatives in up to 99% ee. The reaction could be carried out with a substrate-to-catalyst molar ratio as high as 1000 in undegassed methanol and with no need for inert gas protection.

Cu(I)-Catalyzed Alkynylation of Quinolones

Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

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.

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (?)-cuspareine

A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (?)-cuspareine via enantiospecific construction of the (R)-benzyl 2-formyl-3,4-dihydroquinoline-1(2H)-carboxylate. We have achieved an efficient enantiospe

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

Enantioselective synthesis of tetrahydroquinoline alkaloids (-)-angustureine and (-)-cuspareine from chiral tert-butanesulfinyl imines

The addition of a Grignard reagent to both enantiomeric N-tert-butanesulfinyl imines derived from 3-(2-bromophenyl)propanal 8 proceeded with high diastereoselectivity. The resulting sulfinamides 9 and 12 were easily transformed into tetrahydroquinoline alkaloids (-)-angustureine (4) and (-)-cuspareine (5) after three steps: N-desulfinylation, intramolecular N-arylation and N-methylation.

Enantioselective syntheses of tetrahydroquinolines based on iridium-catalyzed allylic substitutions: Total syntheses of (+)-angustureine and (-)-cuspareine

A protecting-group-free two-step approach for the preparation of tetrahydroquinolines has been developed. The procedure involves a highly regio-and enantioselective intermolecular iridium-catalyzed allylic amination followed by one-pot hydroboration and i

Synthesis of electronically deficient atropisomeric bisphosphine ligands and their application in asymmetric hydrogenation of quinolines

A series of electronically deficient atropisomeric bisphosphine ligands have been synthesized from (S)-MeO-BiPhep. The introduction of electron-withdrawing groups in the ligands had a dramatic influence on both the enantioselectivity and the activity of catalyst. The iridium complex of the MeO-BiPhep-based ligand bearing a trifluoromethanesulfonyl group was successfully applied in the asymmetric hydrogenation of quinolines with ee values of up to 95% and turnover numbers (TON) of up to 14,600. Georg Thieme Verlag Stuttgart, New York.

Asymmetrie hydrogenation with water/silane as the hydrogen source

"Chamical Equation presentd" Water as a hydride source : A new pathway to form metal-hydride bonds has been developed through the reaction of easily available metal-silyl compounds with water. This method has been successfully applied to asymmetric hydrogenation of heteroaromatic compounds with up to 93 % ee under mild autoclave-free conditions (see scheme).