178032-64-9

Upstream product

• 4029-09-8 6,7-dimethoxy-1-phenyl-isoquinoline 
• 10172-51-7 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline 
• 20922-03-6 1-(propan-2-yl)isoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 98-88-4 benzoyl chloride 
• 4118-36-9 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1643770-97-1 (S)-2,2-dimethyl-5-oxo-3-(2-phenylacetyl)imidazolidin-1-yl 2-methoxy-2-phenylacetate 
• 922359-27-1 1-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)pent-4-en-1-one 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 1017594-90-9 (1R)-1-phenyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 100-52-7 benzaldehyde 

Downstream Products

• 853650-68-7 (-)-6,7-dimethoxy-2-(oct-7-ynyl)-1R-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 853650-66-5 (-)-2-(hept-6-ynyl)-6,7-dimethoxy-1R-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 4118-36-9 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

A through halogen bond activation isoquinoline asymmetric hydrogenation method

A through halogen bond activation isoquinoline asymmetric hydrogenation method, the catalyzing system is [...] complex, the activator is a halide. The reaction can be carried out under the following conditions, temperature: 25 - 100 °C; solvent: tetrahydr

A method catalyzed by iridium and used for bidirectional enantioselective synthesis of chiral tetrahydroisoquinoline

A method catalyzed by iridium and used for bidirectional enantioselective synthesis of chiral tetrahydroisoquinoline is provided. A catalysis system adopted by the method is a chiral diphosphine complex of iridium. By utilizing a single chiral source and

Dual Stereocontrol for Enantioselective Hydrogenation of Dihydroisoquinolines Induced by Tuning the Amount of N-Bromosuccinimide

An efficient dual stereocontrol in iridium-catalyzed hydrogenation of 1-substituted 3,4-dihydroisoquinolines was realized by tuning the amount of N-bromosuccinimide using chiral ligand of single configuration, providing both enantiomers of 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 89% ee (S) and 98% ee (R), respectively. Dual activation role of N-bromosuccinimide is proposed to be responsible for the reversal of enantioselectivity under two hydrogenation conditions.

Asymmetric Hydrogenation of Isoquinolines and Pyridines Using Hydrogen Halide Generated in Situ as Activator

By employing halogenide trichloroisocyanuric acid as a traceless activation reagent, a general iridium-catalyzed asymmetric hydrogenation of isoquinolines and pyridines is developed with up to 99% ee. This method avoids tedious steps of installation and removal of the activating groups. The mechanism studies indicated that hydrogen halide generated in situ acted as an activator of isoquinolines and pyridines.

Flow chemistry and polymer-supported pseudoenantiomeric acylating agents enable parallel kinetic resolution of chiral saturated N-heterocycles

Kinetic resolution is a common method to obtain enantioenriched material from a racemic mixture. This process will deliver enantiopure unreacted material when the selectivity factor of the process, s, is greater than 1; however, the scalemic reaction product is often discarded. Parallel kinetic resolution, on the other hand, provides access to two enantioenriched products from a single racemic starting material, but suffers from a variety of practical challenges regarding experimental design that limit its applications. Here, we describe the development of a flow-based system that enables practical parallel kinetic resolution of saturated N-heterocycles. This process provides access to both enantiomers of the starting material in good yield and high enantiopurity; similar results with classical kinetic resolution would require selectivity factors in the range of s = 100. To achieve this, two immobilized quasienantiomeric acylating agents were designed for the asymmetric acylation of racemic saturated N-heterocycles. Using the flow-based system we could efficiently separate, recover and reuse the polymer-supported reagents. The amide products could be readily separated and hydrolysed to the corresponding amines without detectable epimerization.

Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation

A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.

Concise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process

A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.

Asymmetric Transfer Hydrogenation of Imines in Water by Varying the Ratio of Formic Acid to Triethylamine

Asymmetric transfer hydrogenation (ATH) of imines has been performed with variation in formic acid (F) and triethylamine (T) molar ratios in water. The F/T ratio is shown to affect both the reduction rate and enantioselectivity, with the optimum ratio being 1.1 in the ATH of imines with the Rh-(1S,2S)-TsDPEN catalyst. Use of methanol as a cosolvent enhanced reduction activity. A variety of imine substrates have been reduced, affording high yields (94-98%) and good to excellent enantioselectivities (89-98%). In comparison with the common azeotropic F-T system, the reduction with 1.1/1 F/T is faster.

Stereoelectronic basis for the kinetic resolution of n-heterocycles with chiral acylating reagents

The kinetic resolution of N-heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N-heterocycles by using easily prepared reagents. A transition-state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.

Asymmetric transfer hydrogenation of imines in water/methanol co-solvent system and mechanistic investigation by DFT study

Asymmetric transfer hydrogenation of various cyclic imines proceeded efficiently with water/methanol co-solvent media in 20 min with excellent yields and enantioselectivities by employing Rh-TsDPEN catalyst and sodium formate as a hydrogen donor. The role