Enantioselective synthesis of chiral N-arylpyrroles through photoinduced desymmetrization

Abstract

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.