Base-Catalyzed Tandem Michael/Dehydro-Diels–Alder Reaction of α,α-Dicyanoolefins with Electron-Deficient 1,3-Conjugated Enynes: A Facile Entry to Angularly Fused Polycycles

Mingrui Zhang; Junliang Zhang

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Base-Catalyzed Tandem Michael/Dehydro-Diels–Alder Reaction of α,α-Dicyanoolefins with Electron-Deficient 1,3-Conjugated Enynes: A Facile Entry to Angularly Fused Polycycles

机译：碱催化的串联α/α-二氰基烯烃与电子缺陷的1,3-共轭炔烃的迈克尔/脱氢-狄尔斯-阿尔德反应：角熔聚环的便捷进入

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Angularly fused carbocyclic frameworks and their heteroatom-substituted analogues exist in many natural products that display a broad and interesting range of biological activities. Preparation of polycyclic products by cycloaddition reactions have been the long-standing hot topic in the synthetic community. Dehydro-Diels– Alder (DDA) reactions are one class of dehydropericyclic reactions that are derived conceptually by systematic removal of hydrogen atom pairs. A base-promoted tandem Michael addition and DDA reaction of a,a-dicyanoolefins with electron-deficient 1,3-conjugated enynes was realized in which a DDA reaction takes place between the arylalkynes and electron-deficient tetrasubstituted olefin. The control experiments support the stepwise anionic reaction pathway rather than the concerted reaction pathway.

机译：角融合的碳环骨架及其杂原子取代的类似物存在于许多天然产物中，这些产物显示出广泛而有趣的生物活性。通过环加成反应制备多环产物一直是合成界的长期热门话题。脱氢-狄尔斯-阿尔德（DDA）反应是一类脱氢周环反应，从概念上讲是通过系统除去氢原子对而衍生的。实现了碱促进的串联Michael加成反应和α，α-二氰基烯烃与缺电子的1,3-共轭烯炔的DDA反应，其中在芳基炔烃和缺电子的四取代烯烃之间发生了DDA反应。对照实验支持逐步的阴离子反应途径而不是协调的反应途径。

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《Chemistry: A European journal》 |2014年第2期|共6页
作者
Mingrui Zhang; Junliang Zhang;
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正文语种 eng
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carbocyclic; analogues; polycyclic;

机译：碳环;类似物;多环;

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1. Base-Catalyzed Tandem Michael/Dehydro-Diels–Alder Reaction of α,α-Dicyanoolefins with Electron-Deficient 1,3-Conjugated Enynes: A Facile Entry to Angularly Fused Polycycles [J] . Mingrui Zhang, Junliang Zhang Chemistry: A European journal . 2014,第2期

机译：碱催化的串联α/α-二氰基烯烃与电子缺陷的1,3-共轭炔烃的迈克尔/脱氢-狄尔斯-阿尔德反应：角熔聚环的便捷进入
2. Highly Substituted 2,3-Dihydroisoxazoles by Et3N-Catalyzed Tandem Reaction of Electron-Deficient 1,3-Conjugated Enynes with Hydroxylamines [J] . Yu XZ, Du B, Wang K, Organic letters . 2010,第8期

机译：Et3N催化电子缺陷的1,3-共轭炔烃与羟胺的串联反应高度取代的2,3-二氢异恶唑
3. Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters [J] . Mei-Huey Lin, Yu-Chun Chen, Shih-Hao Chiu, Organic & biomolecular chemistry . 2017,第3期

机译：烯丙基溴醇的脱水反应立体选择性地制备共轭（Z）-1,3-烯类化合物和烯类在碱介导的串联烯丙基烯化烯-碳环化反应中与β-酮酸酯的应用
4. Oxidative Ring Expansion Reaction for Synthesis of 7-Membered Ring-fused π-Conjugated Polycycles [C] . Sheng Zhang, Tienan Jin, Masahiro Terada 日本化学会春季年会講演予稿集 . 2018

机译：用于合成7-元环稠合π-共轭多环的氧化环膨胀反应
5. Exploration of the inverse-electron-demand Diels-Alder (IEDDA) reaction. Rapid access to benzocoumarins via IEDDA-driven domino reactions of coumarin-fused electron-deficient dienes with electron-rich dienophiles. [D] . Pottie, Ian R. 2003

机译：逆电子需求Diels-Alder（IEDDA）反应的探索。通过IEDDA驱动的香豆素融合的电子缺陷二烯与富电子的亲二烯体的多米诺反应，可快速获得苯并香豆素。
6. Tandem cross enyne metathesis (CEYM)–intramolecular Diels–Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds [O] . Javier Miró, María Sánchez-Roselló, Álvaro Sanz, 2015

机译：串联交叉烯炔复分解（CEYM）–分子内Diels–Alder反应（IMDAR）。线性双环支架的便捷入门
7. Tandem cross enyne metathesis (CEYM)–intramolecular Diels–Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds [O] . Javier Miró, María Sánchez-Roselló, Álvaro Sanz, 2015

机译：串联交叉炔复分解（CEYm） - 分子内Diels-alder反应（ImDaR）。轻松进入线性双环支架

Base-Catalyzed Tandem Michael/Dehydro-Diels–Alder Reaction of α,α-Dicyanoolefins with Electron-Deficient 1,3-Conjugated Enynes: A Facile Entry to Angularly Fused Polycycles

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