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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Enantioselective [3+2] Cycloaddition of Donor-Acceptor Aziridines and Imines to Construct 2,5-trans-Imidazolidines
Jianglin Qiao1, Shiyu Wang1, Xiaohua Liu1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Abstract:
An enantioselective [3+2] cycloaddition of donor-acceptor aziridines with N-aryl protected imines was developed with a Ni(ClO4 )2 ⋅ 6H2 O/N,N'-dioxide catalyst system, providing a broad range of chiral trans-substituted imidazolidine compounds with good yields and excellent enantioselectivities (up to 99 % yield, up to 98 % ee). Control experiments indicated that the products could offer excellent diastereoselectivities with the control of chiral Ni(II)-N,N'-dioxide complex and the interaction of the substrates. The possible catalytic process was proposed to rationalize the stereocontrol.
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