Enantioselective Reduction of Benzofuranyl Aryl Ketones

Ian Carpenter, Matt Clarke

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Enantioselective transfer hydrogenation of benzofuranyl aryl ketones proceeds with moderate to good enantioselectivity even when the aryl group is not sterically differentiated by ortho-substituents. The best results are obtained with substrates that are functionalised by electron-withdrawing aryl groups that contrast with the electron-rich benzofuran, which is consistent with [Ru-ArC-H]center dot Ar pi interactions acting as a control element. Enantioselective pressure hydrogenation gives lower enantioselectivity irrespective of electronic effects, unless the aryl group is ortho-substituted, in which case up to 86% ee can be realised.

Original languageEnglish
Pages (from-to)65-68
Number of pages4
JournalSynlett
Volume2011
Issue number1
DOIs
Publication statusPublished - Jan 2011

Keywords

  • asymmetric transfer hydrogenation
  • asymmetric hydrogenation
  • heterocyclic ketones
  • asymmetric catalysis
  • electronic control
  • ASYMMETRIC TRANSFER HYDROGENATION
  • 2,3-DIHYDROBENZOFURAN ANALOGS
  • STEREOSELECTIVE HYDROGENATION
  • HETEROAROMATIC KETONES
  • DERIVATIVES
  • COMPLEXES

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