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Updated: May 11, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N,N'-cyclic azomethine imines
Liang Hong1, Ming Kai, Chongyang Wu
1Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000, PR China. hongl@lzu.edu.cn
Abstract:
A new chiral bis-phosphoric acid 3l bearing triple axial chirality was synthesized and applied to effect a highly enantioselective 1,3-dipolar cycloaddition reaction between N,N'-azomethine imines and methyleneindolinones for the creation of chiral spiro[pyrazolidin-3,30-oxindoles] in excellent yields and selectivities. MS experiment and DFT calculation studies prompted us to propose a dual H-bond donor activation mode of bis-phosphoric acid which is different from the traditional phosphoric acid catalysis.
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