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Updated: Mar 3, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Catalytic Asymmetric Kinetic Resolution of 2,2-Disubstituted Styrenyl Aziridines via Ring Opening with Amines
Pei-Jun Yang1,2, Hu Zhang1, Guo-Sheng Zhu1
1MOE Key Laboratory of Functionalized Molecular Solids, Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, 189 South Jiuhua Road, Wuhu, Anhui 241002, China.
Abstract:
We report herein the activation of racemic 2,2-disubstituted styrenyl aziridines by Lewis acid catalysis to undergo ring-opening reactions at a tertiary carbocenter via kinetic resolution with amines. A range of chiral diamine products bearing α-tertiary stereogenic centers as well as enantioenriched aziridines were obtained in good to high yields and enantioselectivities. The synthetic utility of the reaction was demonstrated in various product elaborations, including the synthesis of NK1 antagonist SCH388714.
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