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PreprintCC BY-NC-NDChemRxiv

Construction of Chiral Piperidine Scaffold through an Enantioselective (8+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Azaheptafulvenes

  • Adam Cieśliński1,2
  • Anna Skrzyńska1,2
  • Gonzalo Blay3
  • Carlos Vila3
  • Lukasz Albrecht
  1. 1Institute of Organic Chemistry, Faculty of Chemistry
  2. 2Lodz University of Technology Żeromskiego
  3. 3Departament de Química Orgànica, Facultat de Química, Universitat de València, Av. Vicent Andrés Estellés 19, Burjassot, Spain, 46100
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Abstract

An efficient synthesis of chiral piperidine derivatives via an enantioselective Brønsted base-catalyzed (8+3)-cycloaddition is reported. This strategy employs azaheptafulvenes, which undergo cycloaddition with donor-acceptor cyclopropanes serving as three-carbon building blocks, providing efficient access to a new class of chiral piperidine frameworks. The developed method enables the synthesis of a broad range of chiral piperidine derivatives fused to a seven-membered cycloheptatriene ring with high stereoselectivity, broad substrate scope, and excellent functional group tolerance. Furthermore, transformations of the obtained products were demonstrated, providing access to new chiral piperidine-based frameworks.

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Cite

BibTeXRIS
BibTeX
@misc{cieslinski2026construction,
  title = {{Construction of Chiral Piperidine Scaffold through an Enantioselective (8+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Azaheptafulvenes}},
  author = {Adam Cieśliński and Anna Skrzyńska and Gonzalo Blay and Carlos Vila and Lukasz Albrecht},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008171/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008171/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Construction of Chiral Piperidine Scaffold through an Enantioselective (8+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Azaheptafulvenes
AU  - Adam Cieśliński
AU  - Anna Skrzyńska
AU  - Gonzalo Blay
AU  - Carlos Vila
AU  - Lukasz Albrecht
PY  - 2026
DA  - 2026/09/01
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008171/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008171/v1
AB  - An efficient synthesis of chiral piperidine derivatives via an enantioselective Brønsted base-catalyzed (8+3)-cycloaddition is reported. This strategy employs azaheptafulvenes, which undergo cycloaddition with donor-acceptor cyclopropanes serving as three-carbon building blocks, providing efficient access to a new class of chiral piperidine frameworks. The developed method enables the synthesis of a broad range of chiral piperidine derivatives fused to a seven-membered cycloheptatriene ring with high stereoselectivity, broad substrate scope, and excellent functional group tolerance. Furthermore, transformations of the obtained products were demonstrated, providing access to new chiral piperidine-based frameworks.
ER  -