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Iodocarbocyclization Reaction of β-Ketoesters and Alkynes

José Barluenga,* David Palomas, Eduardo Rubio and José M. González

*Instituto Universitario de Química Organometlica "Enrique Moles"-Unidad Asociada al CSIC, Universidad de Oviedo, Oviedo 33071, Spain, Email: barluengauniovi.es

J. Barluenga, D. Palomas, E. Rubio, J. M. Gonzáles, Org. Lett., 2007, 9, 2823-2826.

DOI: 10.1021/ol0710459 (free Supporting Information)


Abstract

Iodocyclopentenes are formed at room temperature upon iodonium-promoted 5-endo-dig carbocyclization of δ-alkynyl-β-ketoesters with I2. Cyclizations involving terminal and substituted (alkyl, aryl, Br, I) alkynes were accessed.

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Key Words

Cyclopentenes, Iodination


ID: J54-Y2007-2390