Catalytic Asymmetric Carbonylation of Prochiral Sulfonamides via C–H Desymmetrization

Abstract

An enantioselective oxidative C–H/N–H carbonylation process was developed in this work. A bimetallic Pd/Cu-based catalyst system was found to catalyze enantioselective C(sp2)–H carbonylation of prochiral arylsulfonamides via desymmetrization process in the presence of mono-N-protected amino acid ligands. This reaction provides a facile strategy to the stereoselective construction of the lactam-type products, such as isoindoline-1-ones and isoquinoline-1-ones, in good yields and enantioselectivities under balloon pressure with the mixture of CO/O2. The reaction mechanism was rationalized by using density functional theory (DFT) study.