Qiao Jianglin, Wang Shiyu, Liu Xiaohua, Feng Xiaoming
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Chemistry. 2023 Mar 28;29(18):e202203757. doi: 10.1002/chem.202203757. Epub 2023 Feb 24.
An enantioselective [3+2] cycloaddition of donor-acceptor aziridines with N-aryl protected imines was developed with a Ni(ClO ) ⋅ 6H 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.
利用Ni(ClO₄)₂⋅6H₂O/N,N'-二氧化物催化体系,实现了给体-受体氮丙啶与N-芳基保护的亚胺的对映选择性[3+2]环加成反应,得到了一系列具有良好产率和优异对映选择性(产率高达99%,对映体过量值高达98%)的手性反式取代咪唑烷化合物。对照实验表明,在手性Ni(II)-N,N'-二氧化物配合物的控制和底物的相互作用下,产物可提供优异的非对映选择性。提出了可能的催化过程以合理化立体控制。