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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
Access to (Z)-1,2-Endiamides and 1,1-Endiamides via a Base-Promoted Tandem Reaction
Zhenming Zhang1, Bei Fu1, Hui Wang1
1College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, Jiangxi, P. R. China.
Abstract:
An efficient base-promoted tandem reaction between vinyl 1,1-dichlorides and secondary sulfonamides with ynamide as the key intermediate is described. This method provides a facile approach to (Z)-1,2-endiamide and aryl 1,1-endiamide derivatives via the β-hydroamidation of terminal ynamides and the α-hydroamidation of internal ynamides, respectively. This reaction proceeded through double elimination of vinyl chlorides and double addition of nucleophiles to alkynes. In addition, it features readily available starting materials, mild reaction conditions, a broad substrate scope, a wide functional group tolerance, and an operational convenience.
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