Synthesis of α-Ketoamides via Gold(I) Carbene Intermediates
Zuo Zuo Wu, Tapas Adak, Martin C. Dietl, Tao Wang, Chao Hu, Hongwei Shi, Petra Krämer, Matthias Rudolph, Frank Röminger, A. Stephen K. Hashmi
Abstract
α-Ketoamides have been found to be an important functional group in a broad spectrum of inhibitors such as the Corona virus and other viruses. Here we report an unprecedented gold-catalyzed 2-fold reaction of a bromoalkyne with anthranils. Hydrolysis of the initial product then directly leads to α-ketoamides. Water addition to the intermediate α-iminoimidoyl halides delivered α-ketoamides from a broad range of bromoalkynes.
Topics & Concepts
ChemistryCarbeneBroad spectrumHalideHydrolysisCatalysisCombinatorial chemistryOrganic chemistryCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods