Remote C6-Enantioselective C-H Functionalization of 2,3-Disubstituted Indoles through the Dual H-Bonds and pi-pi Interaction Strategy Enabled by CPAs
Remote C6-Enantioselective C-H Functionalization of 2,3-Disubstituted Indoles through the Dual H-Bonds and pi-pi Interaction Strategy Enabled by CPAs
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通过 CPA 实现的双 H-键和 pi-pi 相互作用策略对 2,3-二取代吲哚进行远程 C6-对映选择性 C-H 官能化
DOI：
10.1021/acs.orglett.9b03276
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Zhang Shu-Yu
中科院分区：
文献类型：
--
作者：
Zhou Jia;Zhu Guo-Dong;Wang Le;Tan Fu-Xin;Jiang Wei;Ma Zhi-Gang;Kang Jun-Chen;Hou Si-Hua;Zhang Shu-Yu
首次报道了一种通用的双氢键和π-π相互作用策略，该策略使得2，3-二取代吲哚的C6-选择性C-H远程官能化成为可能。吲哚的N-H键是实现C6功能化的关键，具有良好的产率和对映选择性。此外，这种方法导致许多对映体富集的C6-官能化的吲哚产品在温和的反应条件下，采用不同的亲电试剂的有效建设。初步的细胞增殖研究表明，所合成的手性C6取代吲哚衍生物具有潜在的抗癌活性。
A versatile dual H-bonds and π–π interaction strategy that enables enantioselective remote C6-selective C–H functionalization of 2,3-disubstituted indoles was first reported. The N–H bond of indole was pivotal to achieve the C6 functionalization with excellent yield and enantioselectivity. Furthermore, this methodology leads to the efficient construction of numerous enantioenriched C6-functionalized indole products under mild reaction conditions employing different electrophiles. Preliminary cell proliferation investigations revealed that the synthesized chiral C6-substituted indole derivatives had potential anticancer activities.