134722-07-9Relevant academic research and scientific papers
Asymmetric strecker synthesis of α-arylglycines
Perez-Fuertes, Yolanda,Taylor, James E.,Tickell, David A.,Mahon, Mary F.,Bull, Steven D.,James, Tony D.
, p. 6038 - 6047 (2011/10/08)
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.
Mono-chlorination of electron-rich arylalkyl- and heteroarylalkyl-amines and amino acids using sulfuryl chloride
Yu, Guixue,Mason, Helen J.,Galdi, Kim,Wu, Ximao,Cornelius, Lyndon,Zhao, Ning,Witkus, Michael,Ewing, William R.,Macor, John E.
, p. 403 - 407 (2007/10/03)
Sulfuryl chloride has been used to mono-chlorinate electron-rich arylalkyl- and heteroarylalkyl-amines and amino acids in a mild and efficient one-pot transformation with straightforward purification. Protection of the amines was not needed, and racemization of the chiral amino acids was minimal.
