394740-07-9

Upstream product

• 250665-93-1 [2S,1'S,2'S]-(+)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 250665-98-6 [2S,1'S,2'S]-(+)-2-amino-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 247118-52-1 (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 250666-02-5 (S)-(+)-3,4-(methylenedioxy)phenylglycine 
• 394740-06-8 (2S)-(-)-2-amino-2-(3,4-methylenedioxyphenyl)ethanol 
• 86-51-1 2,3-dimethyoxybenzaldehyde 

Downstream Products

• 394740-13-7 (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol 
• 1026442-56-7 (S)-Benzo[1,3]dioxol-5-yl-[(2,3-dimethoxy-benzyl)-methyl-amino]-acetaldehyde 

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.