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

Chemical Communications Pub Date: 2019-11-01 DOI: 10.1039/C9CC07100H

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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