Enantioselective Hydrogenation and Transfer Hydrogenation of Bulky Ketones Catalysed by a Ruthenium Complex of a Chiral Tridentate Ligand

Maria Belen Diaz Valenzuela, Scott David Phillips, Marcia B. France, Mary E. Gunn, Matt Clarke

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

A study on the enantioselective hydrogenation of tertiary alkyl ketones catalysed by a novel class of tridentate-Ru complex is reported. In contrast to the extensively studied [RuCl2(diphos)(di-primary amine)] Complexes, this new class of hydrogenation catalyst smoothly reduces these less reactive bulk), ketones with up to 949% ee. The same catalyst system can also selectively reduce other potentially problematic substrates such as bulky heterocyclic ketones. Unusually for a pressure hydrogenation catalyst, similar enantioselectivity can be obtained under transfer hydrogenation conditions. The transfer hydrogenations are somewhat slower than the pressure hydrogenations, but this drawback is readily overcome, since we have discovered that a microwave accelerated transfer hydrogenation of the above ketones Occurs within 20 min at about 90 degrees C with similar selectivity to that obtained in the pressure hydrogenation system.

Original languageEnglish
Pages (from-to)1227-1232
Number of pages6
JournalChemistry - A European Journal
Volume15
Issue number5
DOIs
Publication statusPublished - 19 Jan 2009

Keywords

  • asymmetric catalysis
  • heterocyclic ketones
  • hydrogen transfer
  • hydrogenation
  • N,P ligands
  • ASYMMETRIC TRANSFER HYDROGENATION
  • AROMATIC KETONES
  • STEREOSELECTIVE HYDROGENATION
  • HYDRIDE COMPLEXES
  • EFFICIENT
  • IMINES
  • PHOSPHORUS
  • DIHYDROGEN
  • MECHANISM
  • ALCOHOLS

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