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Updated: Sep 18, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Atroposelective N-Allylic Alkylation Enables Construction of Axially Chiral Arylimidazoles
Yangyang Wang1, Kexin Chen1, Hongwei Zhou2
1School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
Abstract:
Atropisomeric pentatomic heterobiaryl scaffolds are challenging to construct due to their configurational lability. Here we report an organocatalytic desymmetrization strategy to synthesize axially chiral arylimidazoles. In the presence of a quinidine organocatalyst, a series of 2-arylimidazoles undergo N-allylic alkylation with Morita-Baylis-Hillman (MBH) carbonates, furnishing enantioenriched arylimidazoles with good to excellent yields (71-98%) and enantioselectivities (79-92%). This process features operational simplicity, mild reaction conditions, the capacity for gram-scale preparation, and straightforward product transformation.
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