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Novel Aromatic Fluoroolefins via Fluoro-Julia-Kocienski Olefination

  作者 ALLENDOERFER NADINE; ESSAYED MAZEN; NIEGER MARTIN; BRAESE STEFAN  
  选自 期刊  Synthesis;  卷期  2010年-20;  页码  3439-3448  
  关联知识点  
 

[摘要]Fluoroolefins, which play an increasingly important role as peptide mimics in pharmaceuticals and as crop protection agents, are generated using a fluoro-Julia-Kocienski olefination. Their preparation can easily be accomplished using a Mitsunobu reaction and subsequent oxidation to generate the required benzothiazolyl sulfones. The key step of this process was the electrophilic alpha-fluorination of the sulfone with N-fluorobenzenesulfonimide. The last stage of the successful synthesis of the fluoroolefins was the modified Julia-Kocienski olefination under basic conditions. Further functionalization was followed with the application of a Suzuki reaction.

 
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