220936-58-3

Upstream product

• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 98-59-9 p-toluenesulfonyl chloride 
• 324027-23-8 2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-benzaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 213686-67-0 (+)-N-<(αS)-2-<<(4R,5R)-4,5-bis(2-methoxypropan-2-yl)-1,3-dioxolan-2-yl>methyl>benzhydryl>-4-methylbenzenesulfonamide 
• 172794-67-1 (4R,5R)-2-(2-Bromo-benzyl)-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3]dioxolane 
• 51608-60-7 phenyl N-tosyl imine 
• 220936-56-1 (S)-(-)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2-dihydroisoquinoline 

Downstream Products

• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol

Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to N-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt3 as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (14), an antagonist of the N-methyl-d-aspartate (NMDA) receptor.

Enantioselective synthesis of 1-aryl-tetrahydroisoquinolines through iridium catalyzed asymmetric hydrogenation

Asymmetric hydrogenation of 1-aryl-3,4-dihydroisoquinolines using the [IrCODCl]2/(R)-3,5-diMe-Synphos catalyst is reported. Under mild reaction conditions, this atom-economical process provides easy access to a variety of enantioenriched 1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives, which are important pharmacophores found in several pharmaceutical drug candidates, in high yields and enantiomeric excesses up to 99% after a single crystallization.

Diastereoselective addition of chiral (2-lithiophenyl)acetaldehyde acetals to various imines as key step in the asymmetric synthesis of 1- aryltetrahydroisoquinolines, part 4

A novel asymmetric synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinolines has been developed. The key step in this synthesis is the diastereoselective addition of homochiral (2-lithiophenyl)acetaldehyde acetals to the sulfonylimine 25 and to the arylimines 28 and 31. The best diastereoselectivity is obtained by addition of the bis(2-methoxypropan-2- yl)-substituted 1,3-dioxolane 6e to benzylidene-p-anisidine (31) with an HPLC-determined diastereomeric ratio 32c/33c = 92.1:7.9. The N-tosyl and the N-(4-methoxyphenyl) groups of the addition products 26d, 27d, 32c, and 33c are cleaved with sodium in liquid ammonia and ammonium cerium(IV) nitrate, respectively, to yield the primary amines 35 and 36. The acid-catalysed cyclization of the sulfonamides 26d and 27d and the carbamates 37 and 38, prepared from 35 and 36, leads to the enantiomerically pure dihydroisoquinolines 40 and 41, respectively. During the cyclization of the sulfonamides 26d, 27d and the carbamates 37, 38 the chiral auxiliary - the diol 39 - is cleaved unchanged and can be recovered in good yields.