Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins
Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins
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金催化邻炔基芳醛与共轭二烯的反应：有效获得高应变四环桥头烯烃
DOI：
10.1002/chem.201601430
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发表时间：
2016-06-27
影响因子：
4.3
通讯作者：
You, Jinmao
中科院分区：
文献类型：
--
作者：
Cao, Ziping;Zhu, Hongbo;You, Jinmao
本文介绍了一种通过易于获取的邻炔基芳醛与共轭二烯反应，前所未有的合成张力四环桥头烯烃的方法。该过程涉及化学和立体选择性的金催化串联分子间[3 + 2]环加成/普林斯（Prins）型关环反应，能够以一种直接的方式构建复杂结构。这种制备反布瑞德（anti - Bredt）化合物的方法在合成方面优于先前报道的方法：该方法易于实施，在温和的实验条件下即可进行，效率高，且底物适用范围广。
An unprecedented access to strained tetracyclic bridgehead alkenes by reaction of easily accessible ortho-alkynylarylaldehydes with conjugated dienes is described. The process involves a chemo-and stereo-selective, gold-catalyzed, tandem intermolecular [3+2] cycloaddition/Prins-type ring-closing reaction that allows generating structural complexity in a straightforward manner. This approach for the preparation of anti-Bredt compounds is synthetically superior to those previously reported: the procedure is easy to implement, operates under mild experimental conditions, is efficient, and exhibits a good substrate scope.