Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels?Alder Reaction
Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels?Alder Reaction
复制标题
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
DOI：
10.1021/acs.orglett.1c03451
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Tanino Keiji
中科院分区：
文献类型：
--
作者：
Ikeuchi Kazutada;Sasage Tomonari;Yamada Gen;Suzuki Takahiro;Tanino Keiji
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（甲硅烷基氧基）-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反应可以提供包括双环[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结构单元。
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.