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Construction of 2,2-Dimethyloxepane Frameworks from Ene-Diols Catalyzed by Metal Catalyst or Brønsted Acid via 7-Endo-Trig Cyclization
Chemical & Pharmaceutical Bulletin ( IF 1.7 ) Pub Date : 2021-09-01 , DOI: 10.1248/cpb.c21-00400
Ryo Murakami 1 , Kakeru Maeda 2 , Fuyuhiko Inagaki 1
Affiliation  

The synthesis of 2,2-dimethyloxepane frameworks based on the 7-endo-trig cyclization of ene-diol using a catalytic amount of metal catalysts (Au, Ag) or Brønsted acid (TfOH) has been developed. Also, the spiro-type dioxabicyclic products were also derived from the diene-diols. For the condition using metal catalysts, the cyclization selectively reacted between the 1,1,3-trisubstituted alkenes and alcohols to form the 2,2-dimethyloxepane frameworks. On the other hand, the TfOH reacted with not only the 1,1,2-trisubstituted alkene, but also the 1-substituted and 1,2-disubstituted alkenes providing the corresponding cyclic ethers, which is quite different from the conditions of the metal catalysts.

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中文翻译:

金属催化剂或布朗斯台德酸催化的烯二醇通过 7-Endo-Trig 环化构建 2,2-二甲基氧杂环庚烷骨架

已经开发了基于使用催化量的金属催化剂(Au、Ag)或布朗斯台德酸(TfOH)的烯二醇的 7 -end-trig环化的 2,2-二甲基氧杂环庚烷骨架的合成。此外,螺型二氧杂二环产物也衍生自二烯二醇。对于使用金属催化剂的条件,环化选择性地在 1,1,3-三取代烯烃和醇之间反应以形成 2,2-二甲基氧杂环庚烷骨架。另一方面,TfOH 不仅与 1,1,2- 三取代烯烃反应,而且与 1-取代和 1,2-二取代烯烃反应,提供相应的环醚,这与金属的条件有很大不同。催化剂。

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更新日期:2021-08-31
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