Selective tandem enyne metathesis for the synthesis of functionalized cycloheptadienes

Steven T. Diver, Daniel A. Clark, Amol A. Kulkarni

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The regio- and site-selective ring expansion of dienes and the regioselective ring expansion of substituted cyclopentenes provide 1,3-cycloheptadienes by enyne metathesis under methylene-free conditions. Site-selectivity results from differential ring strain among two different cycloalkenes in diene reactants. The high regioselectivity found in the ring expansion of tetrahydroindene (THI) is explained on the basis of a selective ring opening by the second generation Grubbs' ruthenium carbene complex. The ring opening of substituted cyclopentenes and cyclopentene contained in a bicyclic ring system was also achieved. The ring expansion of bicyclic dienes provided seven-membered dienes contained in the bicyclo[5.2.0]nonane ring system. Details of the structural analysis are also discussed. A mechanistic analysis is provided to account for the data presented herein.

Original languageEnglish (US)
Pages (from-to)6909-6919
Number of pages11
JournalTetrahedron
Volume64
Issue number29
DOIs
StatePublished - Jul 14 2008

Keywords

  • 1,3-Cycloheptadiene
  • Enyne metathesis
  • Grubbs' catalyst
  • Regioselectivity
  • Ring expansion
  • Ring synthesis
  • Site-selectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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