139224-89-8

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 154902-54-2 (E)-(R)-N-(2-hydroxy-1-phenylethyl)-1-(4-methoxyphenyl)-methylideneamine 
• 143-33-9 sodium cyanide 
• 85803-46-9 (R)-N-(p-Methoxybenzylidene)-2-amino-2-phenylethanol 
• 123-11-5 4-methoxy-benzaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 151-50-8 potassium cyanide 

Downstream Products

• 145058-04-4 methyl (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-methoxyphenyl)ethanoate 
• 75984-71-3 (S)-(4-Methoxy-phenyl)-{[1-phenyl-meth-(E)-ylidene]-amino}-acetic acid methyl ester 
• 24593-48-4 (2S)-2-amino-2-(4-methoxyphenyl)acetic acid 
• 145057-96-1 (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-methoxyphenyl)ethanoic acid 
• 145057-96-1 (R)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-methoxyphenyl)ethanoic acid 
• 1037074-17-1 (S)-(4-Methoxy-phenyl)-{[1-phenyl-meth-(Z)-ylidene]-amino}-acetonitrile 

Relevant academic research and scientific papers

A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines

A simple and economical method for the synthesis of highly functionalised α-amino nitriles, precursors to α-arylglycines with high optical purity is reported. For this purpose, (R) or (S)-2-amino-2- phenylethanol were used as chiral auxiliaries in a 1,3 Strecker reaction. Reactions were studied with a broad range of reagent systems for the generation of cyano nucleophile. Methodology has been extended for the synthesis of (S)-α-(2-iodo-5-nitrophenyl)glycine, (S)-α-(4- methoxyphenyl)glycine and (R)-β-(4-methoxyphenyl)alanine.

α-Phenylglycinol as chiral auxiliary in diastereoselective Strecker synthesis of α-amino acids

The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative clearange make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular mechanics calculations are carried out to explain the observed diastereoselection.

An Efficient and Practical Synthesis of L-α-Amino Acids Using (R)-Phenylglycinol as a Chiral Auxiliary

L-α-Amino acids including L-α-arylglycines were conveniently and stereoselectively synthesized via the α-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide.The stereoselectivity of these α-amino carbonitriles was thermodynamically controlled.

Diastereoselective Strecker Synthesis using α-Phenylglycinol as Chiral Auxiliary

Use of α-phenylglycinol as chiral auxiliary in Strecker synthesis ensures high diastereoselectivity and its easy removal by oxidative cleavage allows large scale preparation of optically active α-amino acids.