title: Asymmetric reduction of ketones by biocatalysis using clementine mandarin (Citrus reticulata) fruit grown in Annaba or by ruthenium catalysis for access to both enantiomers.
abstract: Biocatalytic reduction of prochiral ketones using freshly ripened clementine mandarin (Citrus reticulata) in aqueous medium is reported. High enantioselectivities were observed, especially for the bioreduction of indanone , tetralone , and thiochromanone with respectively 95%, 99%, and 86% enantiomeric excess (ee). Enantioselective bio- and metal-catalyzed reactions were compared. Chiral ruthenium catalysts afforded good asymmetric inductions (>75% ee) in most cases, enantiomeric excesses depending on the nature of substrate and ligand. N-aminoindanol prolinamide was revealed as the best ligand for most ketones. Interestingly, for several substrates both enantiomers could be obtained using either Citrus reticulata or ruthenium complex.
authors.affiliation: Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University, Annaba, Algeria.
authors.forename: Manhel
authors.initials: M
authors.lastname: Bennamane
authors.forename: Saoussen
authors.initials: S
authors.lastname: Zeror
authors.forename: Louisa
authors.initials: L
authors.lastname: Aribi-Zouioueche
mesh_terms: D055162:Biocatalysis; D002384:Catalysis; D002957:Citrus / Q000378:metabolism*; D005638:Fruit; D007659:Ketones / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D012428:Ruthenium
keywords: Citrus reticulate; asymmetric transfer hydrogenation; bioreduction; heteroaryl alcohols; ruthenium