&Beta-Substituted-&Gamma,&Delta-unsaturated amino acids are important synthetic building blocks in organic synthesis and peptidomimetics. The synthesis of syn-&Beta-substituted-&Gamma,&Delta-unsaturated amino acids can be achieved by the Kazmaier-Claisen rearrangement. Optically active products via the Kazmaier-Claisen rearrangement have also been produced in the presence of chiral ligands or using the chiral backbone of a given peptide. However, the asymmetric synthesis of anti-&Beta-substituted-&Gamma,&Delta-unsaturated amino acids has not been well developed. Recently we have successfully synthesized racemic anti-&Beta-substituted-&Gamma,&Delta-unsaturated amino acids with high diastereoselectivities via the Eschenmoser-Claisen rearrangements. We envisioned that a C2 symmetric chiral secondary amine would provide good enantioselectivity in this reaction. Various trans-2,5-disubstituted pyrrolidine auxiliaries were designed and synthesized. The results of the enantioselective Eschenmoser-Claisen rearrangements using these C2 symmetric chiral pyrrolidines will be presented. [Supported by grants from the USPHS and NIDA.]