766537-36-4Relevant academic research and scientific papers
Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives
Atkinson, Rachel C.,Fernández-Nieto, Fernando,Mas Rosell?, Josep,Clayden, Jonathan
, p. 8961 - 8965 (2015/08/03)
Available α-amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′-aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.
Efficient biocatalytic synthesis of highly enantiopure α-alkylated arylglycines and amides
Wang, Mei-Xiang,Lin, Shuan-Jun,Liu, Jun,Zheng, Qi-Yu
, p. 439 - 445 (2007/10/03)
A number of racemic α-alkylarylglycine amides including 1-amino-1-carbamoyl-1,2,3,4-tetrahydronaphthalene underwent efficient biocatalytic hydrolysis under very mild conditions to afford the corresponding (S)-α-alkylarylglycines and (R)-α-alkylarylglycine
