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首页> 外文期刊>Chemistry: A European journal >Samarium diiodide induced cyclizations of γ-,δ-and ε-indolyl ketones: Reductive coupling, intermolecular trapping, and subsequent transformations of indolines
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Samarium diiodide induced cyclizations of γ-,δ-and ε-indolyl ketones: Reductive coupling, intermolecular trapping, and subsequent transformations of indolines

机译：io二碘化物诱导的γ-，δ-和ε-吲哚基酮的环化反应：还原偶联，分子间捕集和二氢吲哚的后续转化

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摘要

This comprehensive study describes our results of samarium diiodide induced 5-exo-trig to 8-exo-trig cyclization/alkylation sequences of 3′-acceptor-substituted indolyl ketones. All cyclization precursors were easily prepared by simple N-alkylation or N-acylation of indole derivatives with the corresponding iodo alkanones, acid chlorides, or lactones. After treatment of indolyl ketones with two equivalents of SmI_2, the generated stabilized carbanionic intermediates were trapped with different electrophiles leading to a variety of highly substituted indoline derivatives in good to very good yields. In general, the cyclization products were obtained as single diastereomers bearing a newly generated quaternary center, a common structural motif in various indole alkaloids. The relative configurations of the products were established by NOE experiments and by single-crystal analysis and follow the rules already established. Furthermore, the obtained products were subjected to a series of chemical transformations, such as oxidation, reduction, and metathesis reactions resulting in a range of interesting synthetic building blocks valuable for further applications.
机译：这项全面的研究描述了我们的结果，即二碘化sa诱导的3'-受体取代的吲哚基酮的5-exo-trig至8-exo-trig环化/烷基化序列。通过将吲哚衍生物与相应的碘代链烷酮，酰氯或内酯进行简单的N-烷基化或N-酰化，可以轻松制备所有环化前体。用两个当量的SmI_2处理吲哚基酮后，生成的稳定化碳负离子中间体被不同的亲电试剂捕获，从而以良好或非常好的收率得到了各种高度取代的二氢吲哚衍生物。通常，环化产物是作为带有一个新生成的四元中心的单一非对映异构体而获得的，该四元中心是各种吲哚生物碱中常见的结构基序。产品的相对构型通过NOE实验和单晶分析确定，并遵循已建立的规则。此外，对获得的产物进行了一系列化学转化，例如氧化，还原和复分解反应，从而产生了一系列有趣的合成基础材料，对进一步的应用有价值。

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