Gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition of captodative dienynes with nitriles:: A new reaction and regioselective direct access to pyridines

被引:111
作者
Barluenga, Jose [1 ]
Fernandez-Rodriguez, Manuel Angel [2 ]
Garcia-Garcia, Patricia [1 ]
Aguilar, Enrique [1 ]
机构
[1] Univ Oviedo, Inst Univ Quim Organometal Enrique Moles, Unidad Asociada, CSIC, E-33006 Oviedo, Spain
[2] CSIC, Inst Invest Quim & Ambientales Barcelona, ES-08034 Barcelona, Spain
关键词
D O I
10.1021/ja7112917
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
For the first time, nitriles are used as 2 Pi electron component in a gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition with captodative enynes leading to the regioselective formation of pyridines.
引用
收藏
页码:2764 / +
页数:3
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