碘作为极性反转催化剂：具有连续立体中心的熔合杂环的合成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-20 DOI:10.1021/acs.orglett.4c03936

Li-Sheng Wang, Yu-Man Song, You Zhou, Yong-Xing Tang, Chun-Yan Wu, Zhi-Cheng Yu, Hui Zhou, Kai-Lu Zheng, An-Xin Wu

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引用次数: 0

摘要

我们报道了一种非常规的i2催化级联反应，用于合成具有融合杂环骨架的角型三醌衍生物，利用胺酮和苯胺作为简单的无环前体。成功的关键在于I2作为极性反转催化剂，改变了漆胺酮α-位置的反应活性，促进了漆胺酮的首次六官能化，并形成了高度密集的连续立体中心。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Iodine as Polarity-Reversal Catalyst: Synthesis of a Fused Heterocycle with Contiguous Stereocenters

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Iodine as Polarity-Reversal Catalyst: Synthesis of a Fused Heterocycle with Contiguous Stereocenters

We report an unconventional I₂-catalyzed cascade reaction for the synthesis of angular triquinane derivatives with a fused heterocycle skeleton, leveraging enaminones and anilines as simple acyclic precursors. The key to success lies in I₂ functioning as a polar-reversal catalyst, which alters the reactivity at the α-position of the enaminone and facilitates the first hexa-functionalization of an enaminone along with the formation of highly congested continuous stereocenters.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.