Construction of 2,3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts through a cascade strategy of N-arylation/cycloaddition/[3,3]-rearrangement
Construction of 2,3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts through a cascade strategy of N-arylation/cycloaddition/[3,3]-rearrangement
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通过N-芳基化/环加成/[3,3]-重排的级联策略从炔基束缚肟和二芳基碘鎓盐构建2,3-季稠合二氢吲哚
DOI：
10.1039/c7gc02844j
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发表时间：
2017-12-21
期刊：
影响因子：
9.8
通讯作者：
Mo, Dong-Liang
中科院分区：
文献类型：
--
作者：
Ma, Xiao-Pan;Li, Kun;Mo, Dong-Liang
在温和的无金属条件下，以炔基肟和二芳基碘鎓盐为原料，以高产率和高的非对映选择性合成了一系列2，3-四元稠合吲哚啉。该反应首先通过选择性的N-芳基化反应得到炔基连接的硝酮，然后区域选择性地进行分子内的（3 + 2）环加成反应，然后进行[3，3]-σ-转移重排反应，以一锅法得到2，3-四元稠合吲哚啉。该方法具有原料易得、价格低廉、多键形成、可规模化制备、融合吲哚啉支架多样性等特点。
A variety of 2,3-quaternary fused indolines could be prepared in good yields with high diastereoselectivity from alkynyl tethered oximes and diaryliodonium salts under mild metal-free conditions. The reaction initially goes through a selective N-arylation to provide alkynyl tethered nitrones and regioselectively undergoes an intramolecular (3 + 2) cycloaddition followed by a [3,3]-sigmatropic rearrangement to afford 2,3-quaternary fused indolines in a one-pot fashion. The method features easily available cheap materials, multiple bond formation, gram scalable preparation and diversity of fused indoline scaffolds.