Synthesis of regio-and stereoisomers of highly functionalized 1,2,3-triazole-substituted cyclopentanes

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Abstract

Highly functionalized regio-and stereoisomers of 1,2,3-triazole-substituted cyclopentanes were prepared in six steps from either bicyclic β-lactam 7 or γ-lactam 23 by 1,3-dipolar cycloaddition of the azido cyclopentanol intermediates with acetylenes. The reactions of azido aminocyclopentanols with non-symmetric acetylenes resulted regioselectively in the corresponding 1,4-disubstitued triazole derivatives under both thermal and Cu(I)-catalysed conditions. These compounds can be regarded as highly functionalized 1,2,3-triazole-modified carbocyclic nucleoside analogues.

Original languageEnglish
Pages (from-to)220-228
Number of pages9
JournalLetters in Organic Chemistry
Volume8
Issue number3
DOIs
Publication statusPublished - Mar 1 2011

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Keywords

  • 1,2,3-triazoles
  • 1,3-dipolar cycloaddition
  • Amino alcohols
  • Azides
  • Carbocyclic nucleosides
  • Click chemistry
  • Enzymes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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