Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade
Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade
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DOI：
10.1021/acs.orglett.7b00794
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发表时间：
2017-04-21
期刊：
影响因子：
5.2
通讯作者：
Giri, Ramesh
中科院分区：
文献类型：
--
作者：
Dhungana, Roshan K.;Shrestha, Bijay;Giri, Ramesh
We disclose a Pd-catalyzed reaction,protocol That regioselectively difunctionalizes unactivated olefins With aryl iodides and tethered enolates. The current method allows the rapid syritheSiS of a variety of 1,3,4-trisubstituted pyrrolidiriones from simple and readily available amides. We further demonstrate this new method's application by postsynthetically modifying the arylacetic acid side chains of two commercial nonsteroidal anti-inflammatory drugs, indomethacin and tolme, tin, to highly decorated 4-benzylpyrrolidinone frameworks. Mechanistic studies reveal that the reaction proceeds via a Heck reaction/enolate cyclization cascade, a process that exploits beta-11 elimination in a constructive mode for regioselective 1,2-difunctionalization of unactivated olefins.
