Enantioselective Transfer Hydrogenation of Ketones Catalyzed by a Manganese Complex Containing an Unsymmetrical Chiral PNP′ Tridentate Ligand

Afrooz Zirakzadeh, Sara R.M.M. de Aguiar, Berthold Stöger, Michael Widhalm, Karl Kirchner

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Abstract

Manganese complexes of the types [Mn(PNP′)(Br)(CO)2] and [Mn(PNP′)(H)(CO)2] containing a tridentate ligand with a planar chiral ferrocene and a centro chiral aliphatic unit were synthesized, characterized, and tested in the enantioselective transfer hydrogenations of 13 ketones. The catalytic reactions proceeded with conversions up to 96 % and ee values up to 86 %. The absolute configuration of all products was determined to be (S). Notably, the presence of dihydrogen (up to 20 bar) did not affect the reduction. On the basis of DFT calculations, preliminary mechanistic details including the origin of the (S) selectivity are presented. The molecular structure of [Mn(PNP′)(Br)(CO)2] was studied by X-ray diffraction.

Original languageEnglish
Pages (from-to)1744-1748
Number of pages5
JournalChemCatChem
Volume9
Issue number10
DOIs
Publication statusPublished - 23 May 2017

Keywords

  • asymmetric synthesis
  • chiral ligands
  • hydride ligands
  • hydrogenation
  • manganese

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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