Diastereoselective palladium-catalyzed C(sp)-H cyanomethylation of amino acid and carboxylic acid derivatives.

In this study, we report an efficient protocol for Pd-catalyzed methylene β-C(sp)-H cyanomethylation of 8-aminoquinoline-directed α-amino acids using inexpensive chloroacetonitrile. Iodoacetonitrile generated from chloroacetonitrile reacts with methylene C(sp)-H bonds of α-amino acids with excellent diastereoselectivity, enabling access to a wide range of important γ-cyano-α-amino acids. Our protocol works well with different amino acid and carboxylic acid derivatives with good chemical yields and high functional group tolerance.