Practical (asymmetric) transfer hydrogenation of ketones catalyzed by manganese with (chiral) diamines ligands

D. Wang (1) , Antoine Bruneau-Voisine (1, 2) , Jean-Baptiste Sortais (1, 2, 3)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCC - Laboratoire de chimie de coordination
3 IUF - Institut Universitaire de France

The reduction of ketones with 2-propanol as reductant was achieved using an in-situ generated catalytic system based on manganese pentacarbonyl bromide, as metal precursor, and ethylenediamine as ligand. The reaction proceeds in high yield at 80 °C, in 3 h, with 0.5 mol% of catalyst. In the presence of chiral (1R,2R)-N,N′-dimethyl-1,2-diphenylethane-1,2-diamine, as the ligand, sterically hindered alcohols were produced with enantiomeric excess up to 90%.

Keywords: Reduction; (1R; N′-dimethyl-1; 2R)-N; 2-diphenylethane-1; 2-diamine; Ketones; Ethylenediamine; Chiral alcohol; Manganese; Chiral diamines; Asymmetric hydrogen transfer

Domains: Chemical Sciences; Catalysis; Chemical Sciences; Organic chemistry

D. Wang, Antoine Bruneau-Voisine, Jean-Baptiste Sortais. Practical (asymmetric) transfer hydrogenation of ketones catalyzed by manganese with (chiral) diamines ligands. Catalysis Communications, 2018, 105, pp.31-36. ⟨10.1016/j.catcom.2017.10.028⟩. ⟨hal-01671636⟩