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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iron-Catalyzed Site- and Regioselective 1,2-Azidoamidations of 1,3-Dienes
Zhen-Yao Dai1, Ilia A Guzei1, Jennifer M Schomaker1
1Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Abstract:
The direct 1,2-azidoamidation of unsaturated precursors represents an advantageous approach for the facile synthesis of β-functionalized azides from readily available starting materials. In this paper, we describe a convenient and mild iron-catalyzed 1,2-azidoamidation of 1,3-dienes that shows excellent functional group compatibility to furnish versatile precursors to 1,2-diamine products with high levels of site, regio-, and stereoselectivity. The reaction is proposed to proceed via a single electron transfer/radical addition/C-N bond formation relay process.
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