Ligand-dependent stereoselective Suzuki-Miyaura cross-coupling reactions of β-enamido triflates

The stereoselective Suzuki-Miyaura cross-coupling of (Z)-beta-enamido triflates is demonstrated. Depending on the nature of the ligand in the palladium catalyst, either retention or inversion of the configuration during the synthesis of beta,beta-diaryl-substituted enamides is observed. Thus, the method provides synthetic access to both isomers of the target enamides from (Z)-beta-enamido triflates.

Automated summary

The stereoselective Suzuki-Miyaura cross-coupling of (Z)-beta-enamido triflates is demonstrated, showing different retention or inversion of configuration in the synthesis of beta,beta-diaryl-substituted enamides depending on the ligand in the palladium catalyst. This method provides access to both isomers of the target enamides from (Z)-beta-enamido triflates.