32886-69-4

Upstream product

• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 102240-27-7 N-(3',4'-dimethoxyphenethyl)-3,4,5-trimethoxybenzamide 
• 3161-21-5 1-(3,4,5-trimethoxylphenyl)-3,4-dihydro-6,7-dimethoxyisoquinoline 
• 1242161-97-2 (1S)-6,7-dimethoxy-3-oxo-1-[3,4,5-(trimethoxyphenyl)]-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Biosynthesis of plant tetrahydroisoquinoline alkaloids through an imine reductase route

Herein, we report a biocatalytic approach to synthesize plant tetrahydroisoquinoline alkaloids (THIQAs) from dihydroisoquinoline (DHIQ) precursors using imine reductases and N-methyltransferase (NMT). The imine reductase IR45 was engineered to significant

Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

A highly efficient and enantioselective access to tetrahydroisoquinoline alkaloids: Asymmetric hydrogenation with an iridium catalyst

Efficient and enantioselective: Using the iodine-bridged dimeric iridium complex [{Ir(H)[(S,S)-(f)-binaphane]}2(μ-I)3] +I- (1) a wide range of tetrahydroisoquinoline alkaloids, including the substructure of the pharmaceutical drug solifenacin, were obtained with excellent enantioselectivities and high turnover numbers (see scheme). Copyright

A general methodology for the enantioselective synthesis of 1-substituted tetrahydroisoquinoline alkaloids

Starting from tricyclic lactam 2, which is easily accessible by cyclocondensation of δ-oxoester 1 with (R)-phenylglycinol, a three-step synthetic route to enantiopure 1-substituted tetrahydroisoquinolines, including 1-alkyl-, 1-aryl-, and 1-benzyltetrahydroisoquinoline alkaloids, as well as the tricyclic alkaloid (-)-crispine A, has been developed. The key step is a stereoselective α-amidoalkylation reaction using the appropriate Grignard reagent.

Asymmetric synthesis. XLI. Totally stereoselective synthesis of 1,3- disubstituted tetrahydroisoquinolines via the CN(R,S) method

Optically active cis- or trans-1,3-disubstituted tetrahydroisoquinolines can be prepared selectively from the same oxazolidine 4. This latter is easily obtained from keto-acid 1 and (R)-(-)-phenylglycinol.