Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes

Olivia Boyd, Gang-Wei Wang, Olga O Sokolova, Adam D J Calow, Sophie M Bertrand, John F Bower

Research output: Contribution to journalArticle (Academic Journal)peer-review

10 Citations (Scopus)
25 Downloads (Pure)

Abstract

Aminocyclopropanes equipped with pendant nucleophiles undergo C-C bond activation triggered carbonylative heterocyclization to provide 8-membered N-heterocycles. In these processes, intramolecular “capture” of a rhodacyclopentanone intermediate by an aryl or N-based nucleophile is followed by C-C or C-N bond forming “collapse” to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.
Original languageEnglish
JournalAngewandte Chemie - International Edition
Early online date4 Oct 2019
DOIs
Publication statusE-pub ahead of print - 4 Oct 2019

Keywords

  • rhodium
  • cyclopropane
  • C-C activation
  • azocane

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