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Stereoselective Synthesis of 2-Carbarnoyl-2-cyanocyclopropanecarboxylates by Tandem Oxidative Cyclization and Neighboring Group-Assisted Decarboxylation

  作者 WANG HUA; FAN RENHUA  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-20;  页码  6994-6997  
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[摘要]In this paper. we report a facile synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates through a tandem iodosobenzene/tetrabutylammonium iodide-induced oxidative cyclization and a subsequent neighboring group-assisted decarboxylation of the Michael adducts of 2-eyanoacetamides with alpha,beta-unsaturated malonates. This method affords the desired highly functionalized cyclopropanes in moderate to good yields and with excellent chastereo selectivities. In addition, the reaction proceeds smoothly under mild conditions and with good functional group tolerance

 
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