Catalytic Asymmetric Carbonylation of Prochiral Sulfonamides via C–H Desymmetrization

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.