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1,3-DIPOLAR CYCLOADDITION OF D-XYLOSE DERIVED NITRONE WITH METHYL ACRYLATE. SYNTHESIS OF CHIRAL PYRROLIDINONES AND PYRROLIDINES

  作者 PODOLAN GABRIEL; FISERA LUBOR; KOZISEK JOZEF; FRONC MAREK  
  选自 期刊  Heterocycles;  卷期  2012年84-1;  页码  683-696  
  关联知识点  
 

[摘要]Several new 3-hydroxysubstituted pyrrolidinones and pyrrolidines with a long-polyolic chain were prepared from chiral isoxazolidines. The cycloaddition of the chiral nitrone 4 derived from D-xylose with methyl acrylate proceeded with very good diastereoselectivity for the anti-trans isoxazolidine 5a. The results show that the method has potential use in the preparation of pyrrolidinones and pyrrolidines containing carbohydrate residues.

 
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