Substrate and Catalyst Effects in the Enantioselective Copper-Catalysed C–H Insertion Reactions of α-Diazo-β-oxo Sulfones

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Abstract

Excellent enantioselectivities of up to 98 % ee are achieved by employing the copper-bis(oxazoline)-NaBARF catalyst system in the C–H insertion reactions of α-diazo-β-oxo sulfones. The influence of variation of the bis(oxazoline) ligand, copper salt, additive and substrate on both the efficiency and the enantioselectivities of these intramolecular C–H insertion reactions has been explored. Optimum enantioselectivities are achieved with phenyl and diphenyl ligands across the substrate series.

Original languageEnglish
Pages (from-to)2277-2289
Number of pages13
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number19
DOIs
Publication statusPublished - 24 May 2018

Keywords

  • Asymmetric synthesis
  • Bis(oxazoline) ligands
  • Copper catalysis
  • C–H insertion
  • Enantioselectivity

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