394739-99-2

Upstream product

• 234089-44-2 (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2-(3,4-dimethoxyphenyl)-N-methylacetamide 
• 147383-98-0 (2S)-(+)-3,4-dimethoxyphenylglycine 
• 250665-97-5 [2S,1'S,2'S]-(+)-2-amino-2-(3,4-dimethoxyphenyl)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 250665-92-0 [2S,1'S,2'S]-(+)-2-(3,4-dimethoxyphenyl)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 114673-69-7 (2S)-(+)-2-amino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-98-1 (2S)-(+)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-97-0 (2S)-(+)-2-(2,3-dimethoxybenzyl)amino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-96-9 (2S)-(-)-2-[(E)-2,3-dimethoxybenzylideneamino]-2-(3,4-dimethoxyphenyl)ethanol 

Relevant academic research and scientific papers

Asymmetric synthesis of arylglycines and their use as chiral templates for the stereocontrolled synthesis of 7,8-disubstituted 3-Aryl-1,2,3,4-tetrahydroisoquinolin-4-ols

A synthetic technique for the asymmetric synthesis of arylglycines has been optimized, reaching the target amino acids in only four steps with good yields and with enantiomeric excesses higher than 99%. The key step consisted of a stereocontrolled electrophilic amination reaction of (S,S)-(+)-pseudoephedrine-based arylacetamide enolates with di-tertbutylazodicarboxylate. The arylglycines thus obtained turned out to be excellent chiral templates for the production of chiral, nonracemic 7,8-disubstituted 3-aryl-1,2,3,4-tetrahydroisoquinolines, through use of a synthetic sequence involving: (1) reduction of the arylglycines to the parent arylglycinols, (2) N-benzylation with appropriately substituted aromatic aldehydes and (3) Swern oxidation followed by acid catalysed cyclization of the obtained a-amino aldehydes.