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


ABSTRACT: 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.

SUBMITTER: Caramenti P 

PROVIDER: S-EPMC6430016 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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

Caramenti Paola P   Declas Nina N   Tessier Romain R   Wodrich Matthew D MD   Waser Jerome J  

Chemical science 20190204 11


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 <i>Z</i>-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 ce  ...[more]

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