Interrupting the nazarov cyclization with indoles
Interrupting the nazarov cyclization with indoles
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DOI：
10.1021/ol801587u
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发表时间：
2008-09-18
期刊：
影响因子：
5.2
通讯作者：
Tius, Marcus A.
中科院分区：
文献类型：
--
作者：
Basak, Ashok K.;Tius, Marcus A.
描述了碳封端的间断纳扎罗夫反应。衍生自炔丙基乙烯基酮的三甲基硅基烯醇醚在远端炔属碳原子处经历选择性质子转移，以提供作为瞬时中间体的丙二烯基乙烯基酮。在吲哚存在下，引发一系列反应，将最初形成的戊二烯基阳离子转化为带有季α碳原子的环戊烯酮。
A carbon-terminated interrupted Nazarov reaction is described. The trimethylsilyl enol ethers derived from propargyl vinyl ketones undergo selective proton transfer at the distal acetylenic carbon atom to provide allenyl vinyl ketones as transient intermediates. In the presence of indoles, a cascade of reactions is initiated that converts the initially formed pentadienyl cations to cyclopentenones bearing a quaternary alpha carbon atom.