N-Hydroxy indoles as flexible substrates in rearrangements - A novel reaction with activated triple bonds

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Abstract

A novel rearrangement of N-hydroxy indole derivatives obtained from addition of N-hydroxy indoles to the activated triple bonds of alkynes was found to coexist with 3,3-sigmatropic rearrangements to the indolic ring. A mechanism involving an intermediate oxaziridinium ring rationalizes the transformation.

Original languageEnglish
Pages (from-to)1173-1176
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number7
DOIs
Publication statusPublished - 13 Feb 2006

Keywords

  • Additions
  • N-Hydroxy indoles
  • Oxaziridinium
  • Rearrangements

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