Simple 1,3-diamines and their application as ligands in ruthenium( <scp>ii</scp> ) catalysts for asymmetric transfer hydrogenation of aryl ketones

  • Facchetti G
  • Gandolfi R
  • Fusè M
 et al. 
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In this research work simple unsym. 1,3-diamines were studied. The synthesis of the diamines started from non-com. available compds. S-5a (I) and S,S-5c (II) were obtained by biocatalysis with non conventional yeast, Rhodotorula rubra MIM 147, with excellent 99% e.e. and d.e. up to 90%. Different approaches of synthesis were applied to the same backbone to study both the steric and electronic effects of the ligands. The reactivity of the corresponding ruthenium complexes was evaluated in the asym. hydrogen transfer redn. of acetophenone as a std. substrate and of other different aryl ketones, highlighting the flexibility of the six membered chelating ring. A screening of the reaction conditions indicated aq. media in the presence of HCOONa as a hydrogen donor to be the best system for overcoming the lack of stereocontrol thus allowing us to obtain 56% e.e. in the redn. of acetophenone with the complex in which the ligand was diamine 1 (III), revealed as the best in terms of reactivity and stereoselectivity also in the redn. of the other different aryl ketones, in particular for α-tetralone (63% e.e.). [on SciFinder(R)]

Author-supplied keywords

  • biocatalysis diamine synthesis Rhodotorula rubra
  • ruthenium diamine catalyst asym transfer hydrogena

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  • Giorgio Facchetti

  • Raffaella Gandolfi

  • Marco Fusè

  • Daniele Zerla

  • Edoardo Cesarotti

  • Michela Pellizzoni

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