Synthesis of Optically Active Amino Acid Derivatives via Dynamic Kinetic Resolution

Abstract

The complete conversion of racemic amino acid amides to optically active amino acid derivatives was accomplished via lipase/palladium-catalyzed dynamic kinetic resolution (DKR). In the DKR, a lipase catalyzes the selective acylation Of L-substrate in the presence of acyl donor while unreacted D-substrate is isomerized by a Pd nanocatalyst to L-substrate. The DKR reactions provided good yields (80-98%) and high enantiomeric excess (95-98% ee). Interestingly, the DKR reactions of phenylglycine amide in the presence of Z-Gly-OMe or Z-Gly-Gly-OMe yielded optically active di- and tripeptide.