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Updated: Dec 27, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Rh-Catalyzed Hydroformylation-Initiated Bicyclization: Construction of Azabicyclic Systems
Wen-Hua Chiou1, Kuo-Hsun Hsu1, Wen-Wei Huang1
1Department of Chemistry, National Chung Hsing University, 250 Kuokuang Road, Taichung 402, Taiwan, R.O.C.
Abstract:
Here, we describe the recent progress toward construction of 1-azabicyclic structures using a domino hydroformylation double cyclization strategy of an amide bearing the trisubstituted alkene functionality. The method provides a rapid and atom-economic access to alkaloid structures under mild conditions, especially for quinolizidine and pyrrolidine-fused azepane skeletons with yields up to 82% and good diastereoselectivity. Subsequent oxidative cleavage conditions are developed for the synthesis of Dendrobatid alkaloid epi-epiquinamide.
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