Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates

Thomas J. Greshock, Raymond Lee Funk

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Abstract

A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 °C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

Original languageEnglish (US)
Pages (from-to)4946-4947
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number15
DOIs
Publication statusPublished - Apr 19 2006

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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