Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers.


Laboratory of Catalysis and Organic Synthesis , Institut des Sciences et Ingénierie Chimique , Ecole Polytechnique Fédérale de Lausanne , Lausanne , Ch-1015 , Switzerland . Email: [Email]


Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ethers based on the use of vinylbenziodoxolone (VBX) reagents. The stable VBX reagents were synthesized by stereoselective addition of N- or O-nucleophiles on the corresponding alkynyl reagents in the presence of a catalytic amount of cesium carbonate. The VBX reagents were used in palladium-catalyzed cross-couplings at room temperature to access Z-enamides and enol ethers.

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