Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system

Megan H Shaw, William G. Whittingham, John Bower

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

19 Citations (Scopus)
406 Downloads (Pure)

Abstract

Urea-directed carbonylative insertion of Rh(I)-catalysts into one of the two proximal C–C bonds of aminocyclopropanes generates rhodacyclopentanone intermediates. These are trapped by N-tethered alkynes to provide a (3+1+2) cycloaddition protocol that accesses N-heterobicyclic enones. Stoichiometric studies on a series of model rhodacyclopentanone complexes outline key structural features and provide a rationale for the efficacy of urea directing groups. A comprehensive evaluation of cycloaddition scope and a ‘second generation’ cationic Rh(I)-system, which provides enhanced yields and reaction rates for challenging substrates, are presented.
Original languageEnglish
Pages (from-to)2731-2741
Number of pages11
JournalTetrahedron
Volume72
Issue number22
Early online date22 Aug 2015
DOIs
Publication statusPublished - 2 Jun 2016

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Rhodium
  • Rhodacyclopentanone
  • Cycloaddition
  • N-Heterocycle
  • Catalysis

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