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Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels–Alder Reaction
Organic Letters ( IF 4.9 ) Pub Date : 2021-11-11 , DOI: 10.1021/acs.orglett.1c03451
Kazutada Ikeuchi 1 , Tomonari Sasage 2 , Gen Yamada 2 , Takahiro Suzuki 1 , Keiji Tanino 1
Affiliation  

We describe a synthetic method for a bicyclo[2.2.1]heptane skeleton with two oxy-functionalized bridgehead carbons. This method involves an intermolecular Diels–Alder reaction using 5,5-disubstituted 1,4-bis(silyloxy)-1,3-cyclopentadienes, the diene structure of which has never been synthesized. Furthermore, the intramolecular Diels–Alder reaction using a diene bearing a dienophile moiety at the C-5 position can provide a tricyclic carbon framework that includes the bicyclo[2.2.1]heptane skeleton. The novel bicyclo[2.2.1]heptane derivatives could be utilized as versatile building blocks for organic synthetic chemistry.

中文翻译:

通过 Diels-Alder 反应合成具有两个氧官能化桥头碳的双环 [2.2.1] 庚烷骨架

我们描述了一种具有两个氧官能化桥头碳的双环 [2.2.1] 庚烷骨架的合成方法。该方法涉及使用 5,5-二取代的 1,4-双(甲硅烷氧基)-1,3-环戊二烯的分子间 Diels-Alder 反应,其二烯结构从未被合成。此外,使用在 C-5 位带有亲二烯体部分的二烯的分子内 Diels-Alder 反应可以提供包含双环 [2.2.1] 庚烷骨架的三环碳骨架。新型双环[2.2.1]庚烷衍生物可用作有机合成化学的通用构件。
更新日期:2021-12-03
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