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Updated: Mar 12, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Breaking aziridines to construct morpholines with a gold(i)-catalyzed tandem ring-opening and cycloisomerization
Shuyao Zhang1, Chuan Shan1, Shuai Zhang1
1Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Abstract:
A convenient synthetic method for the construction of morpholine derivatives from easily available aziridines and propargyl alcohols has been successfully developed. A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(i) catalyst under mild conditions. The gold(i) catalyst served as a π acid and also a σ acid to realize the dual activation of both reactants in this reaction. The obtained unsaturated morpholine products could be easily hydrogenated to achieve target morpholine derivatives with good diastereoselectivities in high yields.
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