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Updated: Jan 15, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Enantioselective Ring-Opening of Cyclic Diaryliodoniums with 3-Hydroxy Benzo[d][1,2,3]triazin-4(3H)-ones: A
Gaimiao Wang1, Chengyu Wang1, Longhui Duan1
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China.
Abstract:
The catalytic asymmetric ring-opening of cyclic diaryliodoniums provides an efficient approach for constructing axial and point chiral molecules. However, previous methodologies have been limited to introducing only a single functional group at the ipso position of the C-I bond. Herein, we report the development of an enantioselective ring-opening reaction of cyclic diaryliodoniums with 3-hydroxybenzo[d][1,2,3]triazin-4(3H)-ones using newly developed chiral bipyridine ligands. This transformation is followed by a stereospecific [2,3]-sigmatropic rearrangement, thereby achieving unprecedented difunctionalization of the aryl ring at both the ipso and ortho positions relative to the original C-I bond.
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