膦介导烯酮与morta - bayis - hillman （MBH）碳酸盐多米诺反应合成双环[n，3,0]烷和偶氮双环[n，3,0]烷

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-08 DOI:10.1021/acs.orglett.5c03510

Yanfei Liu, , , Yong Chen, , , Cheng Deng, , , Hui Yao*, , , Linxuan Li, , , Long Wang, , , Nianyu Huang*, , and , Nengzhong Wang*,

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引用次数: 0

摘要

在此，我们开发了设计的烯酮与MBH碳酸酯的多米诺骨牌反应。该反应要么用化学计量的PBu3进行，要么用硅烷作为还原剂，通过PIII/PV = O氧化还原循环，用R3P = O催化。这种无金属和阶梯经济的方法允许重新合成广泛的双环化合物，包括氮杂-双环[3,3,0]辛烷，双环[3,3,0]辛烷（二醌），氮杂-双环[4,3,0]壬烷和双环[4,3,0]壬烷（氢烷），具有一个桥头堡全碳季位立体中心，收率中等至优异。此外，这种多米诺骨牌反应在同时组装两个环的同时形成了四个新的C-C和C-X键。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of Bicyclo[n,3,0]alkanes and Aza-Bicyclo[n,3,0]alkanes by Phosphine-Mediated Domino Reaction of Enones with Morita–Baylis–Hillman (MBH) Carbonates

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Synthesis of Bicyclo[n,3,0]alkanes and Aza-Bicyclo[n,3,0]alkanes by Phosphine-Mediated Domino Reaction of Enones with Morita–Baylis–Hillman (MBH) Carbonates

Herein, we developed a domino reaction of designed enones with MBH carbonates. The reaction proceeded either with stoichiometric PBu₃ or was catalyzed by R₃P═O via P^III/P^V═O redox cycling by using silane as a reductant. This metal-free and step-economic method allowed for the de novo synthesis of a wide range of bicyclic compounds, including aza-bicyclo[3,3,0]octanes, bicyclo[3,3,0]octanes (diquinanes), aza-bicyclo[4,3,0]nonanes, and bicyclo[4,3,0]nonanes (hydrindanes), bearing one bridgehead all-carbon quaternary stereocenter in moderate to excellent yields. Furthermore, this domino reaction forged four new C–C and C–X bonds while simultaneously assembling two rings.

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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.