Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed[3+2]Cycloaddition:Efficient Synthesis of 1,2,3-Triazolo beta-Hydroxy or beta-Tosylamino Functionality Motif

摘要

A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by"click reaction"using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol% of CuI is described.Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.