Construction of Enantioenriched Quaternary C-Cl Oxindoles through Palladium-Catalyzed Asymmetric Allylic Substitution with Chloroenolates
Construction of Enantioenriched Quaternary C-Cl Oxindoles through Palladium-Catalyzed Asymmetric Allylic Substitution with Chloroenolates
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DOI：
10.1021/acs.joc.3c01811
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发表时间：
2023-10-13
影响因子：
3.6
通讯作者：
Yang，Jianguo
中科院分区：
文献类型：
--
作者：
Huang，Wen;Yang，Jingjie;Yang，Jianguo
在温和的反应条件下，钯催化氯烯酸酯与乙烯基苯并恶嗪酮进行了不对称烯丙化反应，得到了一系列具有光学活性的3,3-二取代氧吲哚，具有一个氯基团和一个线性芳基氨基侧链，收率高达96%。苯环上多功能官能团的耐受性已经得到证明，该方法的实用性通过放大合成和产品衍生化进行了验证。
A palladium-catalyzed asymmetric chloroenolate allylation with vinyl benzoxazinanones under mild reaction conditions has been developed, affording a series of optically active 3,3-disubstituted oxindoles exhibiting a chloro-group and a linear aryl amino side chain in good yields with up to 96% ee. Versatile functional group tolerance on the benzene ring has been demonstrated, and the utility of this method was probed by a scale-up synthesis and highlighted by product derivatizations.