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PreprintCC BYChemRxiv

Enantioselective [3+3] Formal Annulation of Anilines via Carbene Catalysis

  • Daniel Čermák1
  • Vojtěch Dočekal1
  • Ivana Císařová2
  • Jan Veselý1
  1. 1Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, Prague, Czech Republic, 128 00
  2. 2Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, Prague, Czech Republic, 128 00
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Abstract

An efficient preparation of highly enantioenriched cyclic compounds from readily available synthons via stereocontrolled organocatalytic processes remains a significant challenge in modern synthetic chemistry. Herein, we report a highly stereoselective N -heterocyclic carbene (NHC)-catalyzed [3+3] annulation of anilines using α-bromocinnamic aldehydes as convenient acyl-azolium precursors. This protocol offers a straightforward route to valuable chiral lactams in high yields (up to 98%) and excellent enantioselectivities (up to 97:3 er ), featuring broad functional group tolerance. Moreover, the reaction is easily scalable and enables versatile downstream derivatizations, further demonstrating the synthetic utility of the developed methodology.

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Cite

BibTeXRIS
BibTeX
@misc{cermak2026enantioselective,
  title = {{Enantioselective [3+3] Formal Annulation of Anilines via Carbene Catalysis}},
  author = {Daniel Čermák and Vojtěch Dočekal and Ivana Císařová and Jan Veselý},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010507/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010507/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Enantioselective [3+3] Formal Annulation of Anilines via Carbene Catalysis
AU  - Daniel Čermák
AU  - Vojtěch Dočekal
AU  - Ivana Císařová
AU  - Jan Veselý
PY  - 2026
DA  - 2026/10/15
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010507/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010507/v1
AB  - An efficient preparation of highly enantioenriched cyclic compounds from readily available synthons via stereocontrolled organocatalytic processes remains a significant challenge in modern synthetic chemistry. Herein, we report a highly stereoselective N -heterocyclic carbene (NHC)-catalyzed [3+3] annulation of anilines using α-bromocinnamic aldehydes as convenient acyl-azolium precursors. This protocol offers a straightforward route to valuable chiral lactams in high yields (up to 98%) and excellent enantioselectivities (up to 97:3 er ), featuring broad functional group tolerance. Moreover, the reaction is easily scalable and enables versatile downstream derivatizations, further demonstrating the synthetic utility of the developed methodology.
ER  -