Axially chiral molecules are widely found in natural products, bioactive compounds, chiral catalysts or ligands, and functional materials. Therefore, the catalytic atroposelective synthesis of axially chiral molecules has received a substantial amount of attention from chemists in recent years. However, most synthesized axially chiral molecules are restricted to those having a carbon-carbon (C-C) or carbon-nitrogen (C-N) axis, and the catalytic atroposelective synthesis of such molecules has been well established. In stark contrast, the catalytic atroposelective synthesis of N-N axially chiral molecules is not well known. This is because there are specific challenges involved in the catalytic atroposelective synthesis of N-N axially chiral molecules, which mainly include (1) N-N axially chiral molecules have properties, (2) nearly no synthetic strategies are available for the catalytic atroposelective synthesis of N-N axially chiral molecules.<br/>     To address these challenging issues，we designed N-aminoindoles as a class of platform molecules for achieving the highly atroposelective synthesis of N-N axially chiral indoles via the strategy of de novo ring formation. This strategy is applicable for the atroposelective synthesis of N-N axially chiral bispyrroles. More importantly, such N-N axially chiral heterocycles can be derived into chiral organocatalysts with applications in asymmetric catalysis, and displayed potent anticancer activity. This work not only provides a new strategy for the atroposelective synthesis of N-N axially chiral molecules but also offers a new member of the N-N atropisomer family, with promising applications in synthetic and medicinal chemistry.

Organocatalytic atroposelective synthesis of N–N axially chiral indoles and pyrroles by <i>de novo</i> ring formation

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Organocatalytic atroposelective synthesis of N–N axially chiral indoles and pyrroles by de novo ring formation