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The Palladium-Catalyzed Intramolecular Alder-Ene Reactions of O- and N-Linked 1,6-Enynes Incorporating Triethylsilyl Capping Groups
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-11-14 00:00:00 , DOI: 10.1021/acs.joc.7b02355
Jeremy Nugent 1 , Eliška Matoušová 1 , Martin G. Banwell 1 , Anthony C. Willis 1
Affiliation  

A series of O- and N-linked 1,6-enynes (e.g., 11) have been prepared with each subjected to a palladium-catalyzed intramolecular Alder-ene (IMAE) reaction, thus producing the isomeric and cyclic 1,4-diene (e.g., 12). These processes proceed most effectively when a triethylsilyl group is attached to the alkyne moiety and so generating alkenylsilanes that can be manipulated in various useful ways, including via iododesilylation (to give, for example, iodoalkene 62).

中文翻译:

含三乙基甲硅烷基封端基的ON连接的1,6-炔烃的钯催化分子内Alder-Ene反应

已经制备了一系列的ON连接的1,6-烯炔(例如11),每个均进行钯催化的分子内Alder-ene(IMAE)反应,从而产生了异构的环状1,4-二烯(例如12)。当三乙基甲硅烷基连接至炔基部分并因此生成可以以各种有用方式操纵的烯基硅烷时,这些过程将最有效地进行,包括通过碘代去甲硅烷基化反应(例如,得到碘代烯烃62)。
更新日期:2017-11-16
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