对映选择合成
化学
卤化
烯烃
烯烃纤维
电泳剂
邻接
催化作用
药物化学
立体化学
有机化学
作者
Dong Zhang,Maoping Pu,Zhenzhong Liu,Yuqiao Zhou,Zhendong Yang,Xiaohua Liu,Yun‐Dong Wu,Xiaoming Feng
摘要
The textbook alkene halogenation reaction establishes straightforward access to vicinal dihaloalkanes. However, a robust catalytic method for dihalogenizing electron-deficient olefins in an enantioselective manner is still under development, and its mechanism remains controversial. Herein, we disclose efficient regio-, anti-diastereo-, and enantioselective dibromination, bromochlorination, and dichlorination reactions of enones catalyzed by a chiral N,N'-dioxide/Yb(OTf)3 complex. With the combination of electrophilic halogen and halide salts as halogenating agents, an array of homo- and heterodihalogenated derivatives is achieved in moderate to good enantioselectivities. Moreover, DFT calculations reveal that a novel triplet halo-radical pylon intermediate is probable in accounting for the exclusive regio- and anti-diastereoselectivity.
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