Intramolecular Diels-Alder chemistry of 4-vinylimidazoles
Intramolecular Diels-Alder chemistry of 4-vinylimidazoles
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DOI：
10.1039/c0ob00657b
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发表时间：
2011-01-01
影响因子：
3.2
通讯作者：
Lovely, Carl J.
中科院分区：
文献类型：
--
作者：
He, Yong;Krishnamoorthy, Pasupathy;Lovely, Carl J.
研究了4-乙烯基咪唑作为双烯组分参与分子内Diels-Alder反应的情况。在这些研究过程中，评价了影响环加成的几个参数，包括咪唑保护基的性质、亲二烯体的类型和连接基团。这些研究确定氨基连接基通常比醚或酯更有效。在大多数情况下，环加成反应是高度立体选择性的，导致形成来自反过渡态的产物。吡咯-咪唑生物碱当归苷的多取代四氢苯并咪唑核心可以通过使用假二聚4-乙烯基咪唑来构建。
An investigation of 4-vinylimidazoles as diene components in the intramolecular Diels-Alder reaction is described. In the course of these studies several parameters affecting the cycloaddition were evaluated including the nature of the imidazole protecting group, the type of dienophile and the linking group. These investigations established that amino linkers were generally more effective than either ethers or esters. In most cases, the cycloadditions were highly stereoselective, resulting in the formation of products derived from an anti transition state. The polysubstituted tetrahydrobenzimidazole core of the pyrrole-imidazole alkaloid ageliferin can be constructed through the use of pseudo dimeric 4-vinylimidazoles.