Enantioselective synthesis of chiral N-arylpyrroles through photoinduced desymmetrization

作者：Zi‐Wei He, Dong Liang, Jia‐Rong Chen, Ying Cheng, Wen‐Jing Xiao · 发表于：Green Synthesis and Catalysis · 年份：2025 · DOI：10.1016/j.gresc.2025.03.001 · 被引用次数：7 · 研究领域：Axial and Atropisomeric Chirality Synthesis、Molecular spectroscopy and chirality、Chemical synthesis and alkaloids

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.