Chen J, Lu X, Lou W, Ye Y, Jiang H, Zeng W * South China University of Technology, Guangzhou and Chengdu Institute of Biology, P. R. of China
Palladium(II)-Catalyzed Enantioselective Arylation of α-Imino Esters.
J. Org. Chem. 2012;
77: 8541-8548
Key words
palladium - asymmetric arylation - arylglycine derivatives - α-amino acids
Significance
This protocol provides a practical and direct route to chiral arylglycines with high enantioselectivity (up to 99% ee). These derivatives can be easily converted into optically active α-amino acids, which are commonly used as chiral auxiliaries in asymmetric catalysis.
Comment
A palladium(II)-catalyzed asymmetric arylation of N-aryl-α-imino esters using a chiral BOX ligand was developed. This method is applicable to various aromatic boronic acids. A stereochemical model, consistent with experimental results, suggests a re-face attack of the aryl group onto the N-arylimine carbon.
