Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings

Sophie H. Gilbert, José A. Fuentes, David B. Cordes, Alexandra M. Z. Slawin, Matthew L. Clarke

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Abstract

The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures.
Original languageEnglish
Pages (from-to)3071-3076
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number20
Early online date8 May 2020
DOIs
Publication statusPublished - 25 May 2020

Keywords

  • Asymmetric arylation
  • Michael addition
  • Aryl boronic acids
  • Phospholane ligands
  • Asymmetric catalysis

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