Herein, one-pot C−H activation/C−C cleavage for the synthesis of novel spirocyclic β^2,3,3-amino acids, is reported. This approach shows wide substrate scope of CF₃-ynones and ketimines. In addition, several natural products and biologically relevant molecules, prepared by this method, can be further functionalized. Novel dipeptide and tripeptide structures can be successfully assembled with this spirocyclic amino acid.

Abstract

The first synthesis of unnatural β^2,3,3-amino acids with a spirocyclic backbone by one-pot protocol has been presented. This reaction features wide functional group tolerance and feasibility of post-functionalization of natural products and biologically important molecules. Novel dipeptide and tripeptide structures were assembled using this newly developed β^2,3,3-amino acid in high efficiency. The combination of C−H activation and C−C cleavage for the synthesis of β-amino acids would trigger more promising synthetic routes for this compound.