73872-14-7

Upstream product

• 773837-37-9 sodium cyanide 
• 100-52-7 benzaldehyde 
• 35019-66-0 (4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine 
• 143-33-9 sodium cyanide 

Downstream Products

• 29738-09-8 (R)-2-amino-2-phenylpropanoic acid 
• 33875-38-6 (R)-2‐amino‐2‐phenylbutyric acid 
• 6278-95-1 (R)-(+)-α-benzyl-α-phenylglycine 
• 2935-35-5 (S)-2-phenylglycine 

Relevant academic research and scientific papers

Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles

A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity.

Asymmetric strecker synthesis of α-arylglycines

A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure α-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4- methoxyphenyl)ethylamine affords highly crystalline (S,S)-α-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-α-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-α-arylglycines. The enantiopurities of these (S)-α-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by 1H NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.

Nonproteinogenic Amino Acids, I.- A Simple Asymmetric Synthesis of (S)-(+)-2-Phenyl-and (S)-(+)-2-Anisylglycine

A three-step synthesis of optically pure (S)-(+)-2-phenyl-and (S)-(+)-2-anisylglycine (6a and b) is described.Although the yields are only about 50percent, this synthesis nevertheless offers advantages over those involving a racemate cleavage.