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InBr3-Catalyzed Glycosidation of Glycals with Arylamines: An Alternative Approach To Access 4-Aminocyclopent-2-enones

  作者 LI FULONG; DING CHUNYONG; WANG MEINING; YAO QIZHENG; ZHANG AO  
  选自 期刊  Journal of Organic Chemistry;  卷期  2011年76-8;  页码  2820-2827  
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[摘要]To turn side products into major products, a novel strategy to access biologically active 4-aminocyclopent-2-enones was developed. These compounds were originally identified as side products but became major products when 3,5-dimethylpyran-3,4-diol 7a was used as the substrate and 30% InBr3 as the catalyst. Aryl- or heteroarylamines as well as variously substituted glycals can be used in this reaction, and the corresponding 4-aminocyclopent-2-enones were obtained in moderate to good yields. These compounds can be further used to prepare 4-aminocarbocyclic nucleosides.

 
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