Asymmetric synthesis of β,γ-unsaturated α-amino acids via efficient kinetic resolution with cinchona alkaloids

The beta,gamma-unsaturated amino acids are versatile chiral building blocks and biologically interesting compounds. The asymmetric synthesis of beta,gamma-unsaturated amino acids presents a challenging task as these compounds are labile toward racemization as well as the undesirable double bond isomerization. An efficient, general and mild kinetic resolution with readily accessible and fully recyclable cinchona alkaloid catalysts has been developed to provide a reliably useful approach toward optically active beta,gamma-unsaturated amino acids. (C) 2009 Elsevier Ltd. All rights reserved.