Amino acids are ubiquitous building blocks for multiple bioactive modalities such as natural products, peptides, peptidomimetics, antibodies, and hybrid biomolecules. As such, the incorporation of non-canonical amino acids has the ability to not only influence function but also to introduce structural diversity or drug-like properties to chemical matter across modalities. However, use of these frameworks for the purpose of structure-activity relationship (SAR) exploration is often hampered by limited commercial availability and lengthy, non-selective reaction sequences. Consequently, the expedient, robust, and stereoselective synthesis of non-canonical amino acids are of interest to the synthetic community and biomedical fields alike. By utilizing high-throughput experimentation, we have identified robust catalytic systems for the stereoselective synthesis of high-value beta-substituted amino acid derivatives. These methods relied on readily available starting materials and were found to be broad in scope, facilitating the synthesis of novel small molecule and peptide therapeutics.

Transition metal-catalyzed methods for accessing beta-substituted proline derivatives

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.