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Enamides and Enesulfonamides as Nucleophiles: Formation of Complex Ring Systems through a Platinum(II)-Catalyzed Addition/Friedel-Crafts Pathway

TitleEnamides and Enesulfonamides as Nucleophiles: Formation of Complex Ring Systems through a Platinum(II)-Catalyzed Addition/Friedel-Crafts Pathway
Publication TypeJournal Article
Year of Publication2009
AuthorsKozak, JA, Dodd, JM, Harrison, TJ, Jardine, KJ, Patrick, BO, Dake, GR
JournalJournal of Organic Chemistry
Volume74
Pagination6929-6935
Date PublishedSep
Type of ArticleArticle
ISBN Number0022-3263
KeywordsCATALYZED CYCLOISOMERIZATIONS, CLOSING, CYCLIZATION ROUTE, DIASTEREOSELECTIVE SYNTHESIS, ELECTRON-RICH OLEFINS, ENANTIOSELECTIVE REACTIONS, LYCOPODIUM ALKALOIDS, METATHESIS, N-ACYL-ENAMINES, NITROGEN-HETEROCYCLES, REARRANGEMENTS, SKELETAL
Abstract

Cyclic enamine derivatives (enesulfonamides and enamides) tethered to an 1-arylalkynyl fragment undergo a platinum(II)-catalyzed tandem alkyne addition/Friedel-Crafts ring closure to form nitrogen-containing polycyclic structures. Regioselectivity in the initial addition of the enesulfonamide or enamide nucleophile to the platinum(II)-alkyne complex is important. Electron-rich arenes and heterocycles led to the formation of products resulting from an Initial 6-endo cyclization. Twenty-three examples of this process are presented.

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