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<p>C–N/N–N atropisomers constitute pivotal structural elements in privileged scaffolds of natural products, bioactive compounds, chiral ligands, and advanced functional materials. With these wide-ranging utilities, the construction of these axially chiral frameworks has garnered increasing attention from chemists. This review highlights asymmetric annulation as a powerful and efficient strategy to construct such scaffolds, enabling simultaneous aromatic ring formation and axial chirality control in a single step. Recent advances up to August 2025 are summarized, covering both transition metal catalysis (eg., palladium, rhodium, copper, cobalt with chiral ligands) and organocatalysis (e.g., chiral phosphoric acids and <i>N</i>-heterocyclic carbenes). Key methodologies include [4 + 2] cyclizations, ynamide annulations, C–H activation, and annulations involving acroleins or aminocarbonyls, offering versatile routes to diverse C–N and N–N atropisomers with high enantioselectivity. This work provides an integration of catalytic systems previously reviewed in isolation, underscoring the progress in synthetic efficiency and catalytic system diversity.</p> Graphical Abstract <p>This review summarizes recent advances in catalytic asymmetric annulation for the synthesis of C–N and N–N atropisomers. Covering both transition-metal and organocatalytic strategies, it highlights innovative methods that employ <i>de novo</i> annulation to enhance steric hindrance and achieve highly enantioselective construction of chiral axes.</p> <p></p>

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Recent Advances in the Synthesis of C-N/N-N Atropisomers via Asymmetric Annulation

  • 期刊论文

  • 发表日期：

    2026年2月2日

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  • Tong Li,
  • Doudou Leng,
  • Jun-Long Niu,
  • Xu-Hong Hu,
  • Teck-Peng Loh

摘要

C–N/N–N atropisomers constitute pivotal structural elements in privileged scaffolds of natural products, bioactive compounds, chiral ligands, and advanced functional materials. With these wide-ranging utilities, the construction of these axially chiral frameworks has garnered increasing attention from chemists. This review highlights asymmetric annulation as a powerful and efficient strategy to construct such scaffolds, enabling simultaneous aromatic ring formation and axial chirality control in a single step. Recent advances up to August 2025 are summarized, covering both transition metal catalysis (eg., palladium, rhodium, copper, cobalt with chiral ligands) and organocatalysis (e.g., chiral phosphoric acids and N-heterocyclic carbenes). Key methodologies include [4 + 2] cyclizations, ynamide annulations, C–H activation, and annulations involving acroleins or aminocarbonyls, offering versatile routes to diverse C–N and N–N atropisomers with high enantioselectivity. This work provides an integration of catalytic systems previously reviewed in isolation, underscoring the progress in synthetic efficiency and catalytic system diversity.

Graphical Abstract

This review summarizes recent advances in catalytic asymmetric annulation for the synthesis of C–N and N–N atropisomers. Covering both transition-metal and organocatalytic strategies, it highlights innovative methods that employ de novo annulation to enhance steric hindrance and achieve highly enantioselective construction of chiral axes.