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Updated: Jan 3, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes
Shyamsundar Das1, Nakeun Ko, Eunsung Lee
1Department of Nuclear Medicine, Seoul National University College of Medicine, Seoul National University Bundang Hospital, Seongnam, 13620, Republic of Korea. leebc@snu.ac.kr.
Abstract:
Herein, we describe a new transition metal-free Claisen rearrangement for the synthesis of α-substituted 2,4-dienamides. The one-pot, stereoselective three-component cascade reaction between a series of propargyl alcohols, amines, and gem-difluorochloro ethane derivatives afforded various polysubstituted 2,4-dienamides in good yields. This synthetic method for 1,1-captodative dienes, α-substituted 2,4-dienamides, can be utilized for preparing pharmaceutical analogues containing an indolin-2-one or lactone moiety.
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