A concise new synthetic route to furo[2,3-b]indolines has been developed by taking advantage of the reactivity of N-alkenyloxyindole intermediates. These compounds spontaneously undergo [3,3]-sigmatropic rearrangement followed by cyclization to form hemiaminals as single diastereomers. Tin-promoted N-hydroxyindole formation followed by conjugate addition to activated alkynes provides simple and modular access to a diverse array of N-alkenyloxyindoles and their corresponding furo[2,3-b]indolines. Microscale high-throughput experimentation was used to facilitate investigation of the scope and tolerance of this transformation and related studies on the nucleophilic aromatic substitution and rearrangement of N-hydroxyindoles with halogenated arenes have also been evaluated.

中文翻译：

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通过 N-烯氧基吲哚的 [3,3]-Sigmatropic 重排简明合成呋喃 [2,3-b] 吲哚啉

利用 N-链烯氧基吲哚中间体的反应性，开发了一种简洁的呋喃 [2,3-b] 吲哚啉合成路线。这些化合物自发地经历 [3,3]-σ 重排，然后环化形成作为单一非对映异构体的半缩氨酸。锡促进的 N-羟基吲哚形成，然后与活化炔烃的共轭加成提供了对各种 N-烯氧基吲哚及其相应呋喃 [2,3-b] 吲哚啉的简单和模块化的访问。微型高通量实验用于促进对这种转化的范围和耐受性的研究，并且还评估了对 N-羟基吲哚与卤代芳烃的亲核芳香取代和重排的相关研究。