250665-99-7

Upstream product

• 250665-95-3 [2S,1'S,2'S]-(+)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4,5-trimethoxyphenyl)acetamide 

Downstream Products

• 58716-92-0 (2S)-(+)-3,4,5-trimethoxyphenylglycine 
• 474126-01-7 (2S)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanone 
• 761395-52-2 (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethanol 

Relevant academic research and scientific papers

Asymmetric synthesis of arylglycine amino acids using (S,S)-(+)- pseudoephedrine derived amides

Arylglycine aminoacids were obtained in good yields and with enantiomeric excesses higher than 99% by using an asymmetric amination reaction protocol on (S,S)-(+)-pseudoephedrine based arylacetamide enolates with di-tert-butylazodicarboxylate. Subsequent hydrazinolysis and hydrolysis yielded the target aminoacids.

Asymmetric synthesis of 1,2-diaryl-2-amino ethanols

A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetam

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.