Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Megan H. Shaw, Ekaterina Y. Melikhova, Daniel P. Kloer, William G. Whittingham, John F. Bower*

*Corresponding author for this work

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

82 Citations (Scopus)

Abstract

Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

Original languageEnglish
Pages (from-to)4992-4995
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number13
DOIs
Publication statusPublished - 2 Apr 2013

Structured keywords

  • BCS and TECS CDTs

Keywords

  • C-C BOND
  • CARBON-CARBON
  • ORGANIC-SYNTHESIS
  • ORGANOMETALLIC CHEMISTRY
  • CYCLOADDITION REACTION
  • ATOM ECONOMY
  • ACTIVATION
  • INSERTION
  • METALS
  • CARBOCYCLIZATION

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