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Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes

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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.

Graphical abstract: Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes

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Publication details

The article was received on 11 Sep 2019, accepted on 30 Oct 2019 and first published on 01 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC07100H
Chem. Commun., 2019, Advance Article

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    Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes

    S. Das, N. Ko, E. Lee, S. E. Kim and B. C. Lee, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC07100H

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