Stereospecific [3+2] Cycloaddition of Chiral Arylallenes with C,N-Cyclic Azomethine Imines.

De Wang, Xinyu Liu, Manjaly John Ajitha, Zhixin Liu, Yongyi Hu, Kuo-Wei Huang

Research output: Contribution to journalArticlepeer-review


A novel α,β-regioselective [3+2] cycloaddition reaction of arylallene with C,N-cyclic azomethine imine is reported. The axial-to-central chirality transfer phenomenon has been disclosed with chiral allenes in the reaction. The wide substrate scope, including different functional groups and natural products, reveals the generality of the methodology. Both experiments and density functional theory calculations have been used to elucidate a plausible mechanism.
Original languageEnglish (US)
JournalOrganic Letters
StatePublished - Apr 28 2023

Bibliographical note

KAUST Repository Item: Exported on 2023-05-02
Acknowledgements: The authors thank the Fundamental Research Funds for the Central Universities in China, NSFC (U1906212), and the Natural Science Foundation of Shandong Province (ZR2021QB011) for financial support. The authors also acknowledge financial support and the service of Ibex, Shaheen 2 High Performance Computing Facilities from King Abdullah University of Science and Technology.

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry


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