Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines

Roohollah Kazem Shiroodi, Claudia I. Rivera Vera, Alexander S. Dudnik, Vladimir Gevorgyan

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

A novel gold-catalyzed divergent synthesis of furans and pyrroles employing readily available homopropargylic aldehydes and imines has been developed. The regiochemical outcome of this reaction is dependent on the substituent on the terminal alkyne of substrate. Thus, substrates possessing alkyl and aryl substituent at the alkyne moiety produce 2,3,5-substituted furans and pyrroles via a migratory cycloisomerization reaction. Whereas, their silicon analogues are capable of undergoing a double migratory process leading to 2,3,4-substituted heterocycles.

Original languageEnglish (US)
Pages (from-to)3251-3254
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - Jun 3 2015
Externally publishedYes

Keywords

  • Cycloisomerization
  • Double migration
  • Gold catalyst
  • Heterocycles
  • Silicon migration

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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