Ag-Catalyzed Asymmetric Interrupted Barton–Zard Reaction Enabling the Enantioselective Dearomatization of 2- and 3-Nitroindoles
Ag-Catalyzed Asymmetric Interrupted Barton–Zard Reaction Enabling the Enantioselective Dearomatization of 2- and 3-Nitroindoles
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Ag 催化的不对称中断 Barton-Zard 反应实现 2- 和 3-硝基吲哚的对映选择性脱芳构化
DOI：
10.1021/acs.orglett.1c04036
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Yong You
中科院分区：
文献类型：
--
作者：
Wei-Cheng Yuan;Xin-Meng Chen;Jian-Qiang Zhao;Yan-Ping Zhang;Zhen-Hua Wang;Yong You
我们揭示了一种银催化的α-芳基取代异氰乙酸酯与2-和3-硝基吲哚的不对称中断巴顿-扎德反应，该反应使硝基吲哚脱芳化，从而可以快速获得一系列具有光学活性的四氢吡咯[3,4-b]吲哚衍生物，这些衍生物具有三个连续的立体中心，包括两个四取代的手性碳原子，其结果很好（产率高达99%，dr: 91， ee为96%）。该方案的合成潜力通过克级反应和产品的多功能转化得到了展示。
We disclose a Ag-catalyzed asymmetric interrupted Barton–Zard reaction of α-aryl-substituted isocyanoacetates with 2- and 3-nitroindoles, which enables the dearomatization of nitroindoles and hence offers rapid access to an array of optically active tetrahydropyrrolo[3,4-b]indole derivatives bearing three contiguous stereogenic centers, including two tetrasubstituted chiral carbon atoms with pretty outcomes (up to 99% yield, 91:9 dr, and 96% ee). The synthetic potential of the protocol was showcased by the gram-scale reaction and versatile transformations of the product.