Rhodium-Catalyzed C-H Alkylation for the Stereoselective Synthesis of β,β-Disubstituted Dehydroamino-Acid Motifs

In this article, we describe the stereoselective formation of beta,beta-disubstituted dehydroamino acids (Delta AAs) in peptides using a cationic rhodium catalyst and methyl trifluoroborate salt. Using this approach, an alkyl group was directly installed on a beta-monosubstituted Delta AA in the peptide chain and both isomers of dehydroisoleucine, an important yet usually inaccessible Delta AA, were successfully obtained.

Automated summary

In this study, a cationic rhodium catalyst and methyl trifluoroborate salt were used to achieve the stereoselective formation of beta,beta-disubstituted dehydroamino acids (ΔAAs) in peptides. This method allowed the direct installation of an alkyl group on a beta-monosubstituted ΔAA in the peptide chain, leading to the successful synthesis of both isomers of dehydroisoleucine, which is an important yet usually inaccessible ΔAA.