Catalytic Enantioselective Dearomatization/Rearomatization of 2-Nitroindoles to Access 3-Indolyl-3′-Aryl-/Alkyloxindoles: Application in the Formal Synthesis of Cyclotryptamine Alkaloids
Catalytic Enantioselective Dearomatization/Rearomatization of 2-Nitroindoles to Access 3-Indolyl-3′-Aryl-/Alkyloxindoles: Application in the Formal Synthesis of Cyclotryptamine Alkaloids
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2-硝基吲哚的催化对映选择性脱芳构化/重芳构化得到 3-吲哚基-3-芳基-/烷基吲哚：在环色胺生物碱的正式合成中的应用
DOI：
10.1021/acs.orglett.0c02350
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发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
Zhen-Hua Wang
中科院分区：
文献类型：
--
作者：
Wei-Cheng Yuan;Xiao-Jian Zhou;Jian-Qiang Zhao;Yong-Zheng Chen;Yong You;Zhen-Hua Wang
The first catalytic enantioselective dearomatization/rearomatization of 2-nitroindoles triggered by the Michael addition of 3-monosubstituted oxindoles was established. A wide range of 3-indolyl-3′-alkyloxindoles (up to 99% yield, 97% ee) and 3-indolyl-3′-aryloxindoles (up to 95% yield, 99% ee) were obtained by using an organocatalyst. This method provides an unprecedented strategy to access structurally diverse 3,3′-disubstituted oxindoles bearing a sterically congested triaryl-containing all-carbon quaternary stereocenter. The utility of this approach was verified by the formal synthesis of cyclotryptamine alkaloids.
