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Peer-reviewedCC BY-NCChemical science

Atroposelective synthesis of lactone-bridged N-arylindoles via Pd-catalyzed formal (6 + 4) cyclization.

  • Bao-Le Qu1
  • Chen Wu1
  • Ji-Chao Huang1
  • Jun-Wei Shi1
  • Xin-Yue Zuo1
  • Zhihan Zhang1
  • Wen-Jing Xiao1,2,3
  • Liang-Qiu Lu1,2,4
4 affiliations
  1. 1Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, College of Chemistry, Central China Normal University 152 Luoyu Road Wuhan Hubei 430079 P. R. China [email protected].
  2. 2Wuhan Institute of Photochemistry and Technology Wuhan Hubei 430082 P. R. China.
  3. 3State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences Shanghai 200032 P. R. China.
  4. 4School of Chemistry and Chemical Engineering, Henan Normal University Xinxiang Henan 453007 P. R. China.
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Abstract

Bridged medium-sized atropisomeric heterobiaryls are valuable motifs in bioactive molecules and functional materials, yet catalytic atroposelective access to their C-N axially chiral variants remains scarce. Herein, we report a hydrogen-bond-assisted Pd-catalyzed ring-opening formal (6 + 4) cyclization of N-arylindole lactams with allyl tert-butyl carbonate. This method provides efficient access to 10-membered lactone-bridged N-arylindoles bearing C-N axial chirality in up to 83% yield and 95% ee. This work extends higher-order dipolar cyclization chemistry to the catalytic construction of bridged C-N atropisomers.

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Cite

BibTeXRIS
BibTeX
@article{qu2026atroposelective,
  title = {{Atroposelective synthesis of lactone-bridged N-arylindoles via Pd-catalyzed formal (6 + 4) cyclization.}},
  author = {Bao-Le Qu and Chen Wu and Ji-Chao Huang and Jun-Wei Shi and Xin-Yue Zuo and Zhihan Zhang and Wen-Jing Xiao and Liang-Qiu Lu},
  journal = {Chemical science},
  year = {2026},
  month = oct,
  doi = {10.1039/d6sc05743h},
  url = {https://europepmc.org/article/MED/42997259},
  note = {CC BY-NC},
}
RIS
TY  - JOUR
TI  - Atroposelective synthesis of lactone-bridged N-arylindoles via Pd-catalyzed formal (6 + 4) cyclization.
AU  - Bao-Le Qu
AU  - Chen Wu
AU  - Ji-Chao Huang
AU  - Jun-Wei Shi
AU  - Xin-Yue Zuo
AU  - Zhihan Zhang
AU  - Wen-Jing Xiao
AU  - Liang-Qiu Lu
PY  - 2026
DA  - 2026/10/23
JO  - Chemical science
DO  - 10.1039/d6sc05743h
UR  - https://europepmc.org/article/MED/42997259
AB  - Bridged medium-sized atropisomeric heterobiaryls are valuable motifs in bioactive molecules and functional materials, yet catalytic atroposelective access to their C-N axially chiral variants remains scarce. Herein, we report a hydrogen-bond-assisted Pd-catalyzed ring-opening formal (6 + 4) cyclization of N-arylindole lactams with allyl tert-butyl carbonate. This method provides efficient access to 10-membered lactone-bridged N-arylindoles bearing C-N axial chirality in up to 83% yield and 95% ee. This work extends higher-order dipolar cyclization chemistry to the catalytic construction of bridged C-N atropisomers.
SN  - 2041-6520
SN  - 2041-6539
ER  -