Citation: Yi Ma, Yu-Zhen Zhang, Qi-Tao Lu, Ming-Shu Li, Quan Cai. Kinetic resolution of inherently chiral tribenzocyclooctanones via enantioselective condensation with phenylhydrazines[J]. Chinese Chemical Letters, ;2026, 37(12): 112515. doi: 10.1016/j.cclet.2026.112515 shu

Kinetic resolution of inherently chiral tribenzocyclooctanones via enantioselective condensation with phenylhydrazines

Department of Chemistry, Research Center for Molecular Recognition and Synthesis, State Key Laboratory of Green Chemical Synthesis and Conversion, Fudan University, Shanghai 200433, China

quan_cai@fudan.edu.cn

Received Date: 19 November 2025
Revised Date: 3 February 2026
Accepted Date: 10 February 2026
Available Online: 11 February 2026

Figures(4)

Inherently chiral octagon-containing polycyclic arenes have attracted significant attention due to their broad applications in asymmetric catalysis and material science. However, the catalytic enantioselective construction of all-carbon-based eight-membered ring scaffolds with inherent chirality remains elusive. Herein, we report the efficient kinetic resolution of racemic tribenzocyclooctanones via chiral phosphoric acid-catalyzed condensation with phenylhydrazines. Through this approach, a variety of hydrazones were obtained with high enantioselectivities, which could be converted into tribenzocyclooctaindoles without loss of enantiopurity via Fischer indolization under acidic conditions. The synthetic utility of this method was further demonstrated by the facile preparation of inherently chiral tribenzocyclooctatetraenes and tetraphenylenes from recovered tribenzocyclooctanones in high enantiopurity. DFT calculations were performed to elucidate the notable thermodynamic stability associated with the inherent chirality of these tribenzo-fused eight-membered carbocycles.
- Inherent chirality,
- Tribenzocyclooctanones,
- Kinetic resolution,
- Chiral phosphoric acid,
- Asymmetric condensation
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