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Updated: Jan 13, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Enantioselective rapid assembly of bis-heterocycles by sequential palladium-catalyzed aza-Heck cyclization coupling
Lei Wang1, Shuaijie Wu1, Wenyu Zhang1
1School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
Abstract:
A highly efficient palladium-catalyzed enantioselective aza-Heck-catalyzed cyclization coupling reaction of alkyne-tethered oxygen- and nitrogen-centered nucleophiles is reported. This protocol enables versatile access to chiral isoindolinone-linked benzofuran and indole bis-heterocyclic derivatives bearing a quaternary stereogenic center in good yields with high enantioselectivities. A sterically demanding, electron-rich (S)-(+)-1,1'-Bi-2-naphthol (BINOL)-derived phosphoramidite ligand provides excellent control over both chemoselectivity and enantioselectivity. Density functional theory calculations were used to elucidate the reaction mechanism and the origin of enantioselectivity. Moreover, these bis-heterocycles exhibited promising antimicrobial activity.
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