Enantioselective synthesis of chiral N-arylpyrroles through photoinduced desymmetrization

The C–N axial chirality is widely present in natural products, bioactive molecules, and chiral ligands. Catalytic asymmetric construction of C–N axially chiral compounds is a challenging task due to the lower rotational barriers of the C–N bond. Here, we report catalytic asymmetric Minisci reaction of prochiral N -arylpyrroles with α -amino acid-derived redox-active esters to produce enantiomerically enriched N -arylpyrroles with a C–N axis by dual photoredox and chiral phosphoric acid catalysis. The desymmetrization strategy achieved a variety of N -arylpyrroles with generally good diastereo- and enantioselectivities. A photoinduced desymmetrization protocol for the construction of chiral N -arylpyrroles with a C–N axis is described.