Enantioselective synthesis of beta-amino acids for inclusion into natural products

Abstract

Reported herein is the analysis of methods to synthesize beta-amino acids for the use in natural product synthesis. Three syntheses were attempted to create the necessary beta-enamide intermediates, however, only one method was found to be consistently successful in producing the desired product. This method consisted of two-steps utilizing acyl chlorides to functionalize the amine group and create six desired beta-enamide. Hydrogenations of each of these molecules were then attempted using (S)-Binapine coupled with Ni(OAc)2 to determine the compatibility of this molecule with beta-enamides with various substituents. It was determined that a complex of (S)-binapine and Ni(OAc)2 was only successful with two of the six molecules. Further investigation will be completed to determine the differences between metal ligands and the abilities of other ligands to complete these hydrogenations.