Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles,Organic Letters

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Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-12 , DOI: 10.1021/acs.orglett.4c03106
Vitaly V Shorokhov ₁ , Beauty K Chabuka ₂ , Timur P Tikhonov ₁ , Anastasia V Filippova ₁ , Sergey S Zhokhov ₁ , Victor A Tafeenko ₁ , Ivan A Andreev ₃ , Nina K Ratmanova ₃ , Maxim G Uchuskin ₄ , Igor V Trushkov ₅ , Igor V Alabugin ₂ , Olga A Ivanova ₁

Affiliation

Here, we present a new approach for the activation of donor–acceptor cyclopropanes in ring-opening reactions, which does not require the use of a Lewis or Brønsted acid as a catalyst. Donor–acceptor cyclopropanes containing a phenolic group as the donor undergo deprotonation and isomerization to form the corresponding quinone methides. This innovative strategy was applied to achieve (4 + 1)-annulation of cyclopropanes with sulfur ylides, affording functionalized dihydrobenzofurans. Additionally, the generated ortho- and para-(aza)quinone methides can be trapped by various CH-acids.

中文翻译：

将应变释放转化为芳香度损失以激活供体-受体环丙烷：生成 C-亲核试剂的醌甲基化物陷阱

在这里，我们提出了一种在开环反应中活化供体-受体环丙烷的新方法，该方法不需要使用路易斯酸或布朗斯台德酸作为催化剂。含有酚基作为供体的供体-受体环丙烷进行去质子化和异构化，形成相应的醌甲基化物。这一创新策略用于实现环丙烷与硫叶立德的 (4 + 1) 环化，得到功能化的二氢苯并呋喃。此外，生成的邻-和对-(氮杂)醌甲基化物可以被各种CH-酸捕获。

更新日期：2024-09-12

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