环加成
化学
环丙烷
芳基
立体选择性
硝基
光催化
动力学分辨率
催化作用
光化学
对映选择合成
组合化学
立体化学
戒指(化学)
有机化学
光催化
烷基
作者
Yao Xu,Haixiang Gao,Chengkai Pan,Yue Shi,Chi Zhang,Genping Huang,Chao Feng
标识
DOI:10.1002/anie.202310671
摘要
By resorting to the principle of remote activation, we herein demonstrate the first photoredox catalyzed (3+3) dipolar cycloaddition of nitrones with aryl cyclopropanes. Key to the fidelity of the reaction resides in a facile manner of substrate activation by single-electron transfer (SET) oxidation with photoredox catalysis, and the reaction takes place through a stepwise cascade encompassing a three-electron-type nucleophilic substitution triggered cyclopropane ring-opening and a diastereoselective 6-endo-trig radical cyclization manifold. The reaction proceeds under mild conditions with excellent regio- and stereoselectivity, nicely complementing the well-developed Lewis acid catalyzed cycloaddition of donor-acceptor cyclopropanes. Other merits of the protocol include wide scope of aryl cyclopropanes with diversified substitution patterns and good functional-group compatibility. A mechanism involving an aryl radical cation promoted remote activation mode was also proposed and supported by mechanistic experiments.
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