Reactivity and rearrangements of dialkyl- and diarylvinylsulfonium salts with indole-2- and pyrrole-2-carboxaldehydes

Yufeng Wang, Weihong Zhang, Vincent J. Colandrea, Leslie S. Jimenez

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

Various dialkyl- and diarylvinylsulfonium salts react with indole-2- carboxaldehydes in the presence of sodium hydride and sodium azide to form tricyclic azido alcohols analogous to 2. With pyrrole-2-carboxaldehyde, [2,3] sigmatropic and other rearrangements occur except in the case of diphenylvinylsulfonium trifluoromethanesulfonate where the annulation reaction does take place to give a low yield of 29.

Original languageEnglish (US)
Pages (from-to)10659-10672
Number of pages14
JournalTetrahedron
Volume55
Issue number35
DOIs
StatePublished - Aug 27 1999

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Bicyclic heterocyclic compounds
  • Natural products
  • Rearrangements
  • Sulfonium salts

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