Enantioselective ketoester reductions in water: a comparison between microorganism- and ruthenium-catalyzed reactions

Zeror, Saoussen; Collin, Jacqueline; Fiaud, Jean‐Claude; Aribi‐Zouioueche, Louisa

doi:10.1016/j.tetasy.2010.05.014

Cited by 22 publications

(9 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…28 It may be noted that comparative studies on the enantioselective reductions of a variety ketoesters by bio-and water-soluble chiral ruthenium catalysts have recently been reported. 29 However, for MPV hydrogenation with these ruthenium catalysts the maximum enantioselectivity was e12%.…”

Section: Introductionmentioning

confidence: 93%

Kinetic and Scanning Transmission Electron Microscopy Investigations on a MCM-41 Supported Cluster Derived Enantioselective Ruthenium Nanocatalyst

et al. 2011

View full text Add to dashboard Cite

The asymmetric hydrogenation of methyl pyruvate to methyl lactate, by cinchonidium functionalized MCM-41 supported [Ru4(μ-H)3(CO)12]− as the precatalyst has been studied kinetically and by scanning transmission electron microscopy (STEM). Existence of an induction time and two competitive equilibriums are inferred from the time monitored conversion data. Steady state approximation gives a poor fit, but a kinetic model (Eley−Rideal) consisting of a fast equilibrium between methyl pyruvate and the catalyst, a slow one between the catalyst and dihydrogen, and a rate determining reaction between the latter and methyl pyruvate, accurately simulates the time monitored conversion profiles. The model suggests that on increasing the methyl pyruvate concentration there is a change in the stoichiometry of the equilibrium between the catalyst and the methyl pyruvate. The change in enantioselectivity with time can also be accurately simulated by assuming enantiomeric excess to be proportional to the rate constant for methyl lactate formation. Both kinetic and STEM data strongly suggest that in the fresh catalyst the bare metal cluster framework is retained, and under the catalytic conditions agglomeration of the subnano sized clusters leading to the formation of nanoparticles of ruthenium is a relatively slow process. A hypothetical enantionface selection mechanism consistent with the empirical rate law, previous reports, and other experimental evidence is proposed.

show abstract

Section: Introductionmentioning

confidence: 93%

Kinetic and Scanning Transmission Electron Microscopy Investigations on a MCM-41 Supported Cluster Derived Enantioselective Ruthenium Nanocatalyst

et al. 2011

View full text Add to dashboard Cite

show abstract

“…We compared the enantioselective reduction of ketoesters by Saccharomyces cerevisiae ‐ and ruthenium‐catalyzed reactions in water. The highest enantiomeric excess ( ee) for the reduction of α‐and β‐ketoesters was obtained with Saccharomyces cerevisiae . Interestingly, for several substrates both enantiomers of the hydroxyesters were obtained according either to the catalytic method or to the structure of the ligand.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Reduction of Ketones by Biocatalysis Using Clementine Mandarin (Citrus reticulata) Fruit Grown in Annaba or by Ruthenium Catalysis for Access to Both Enantiomers

2014

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…In the course of our previous investigations, the comparison between enantioselective bio-and metal-catalyzed reactions has been examined. We have compared the enantioselective reduction of ketoesters by Saccharomyces cerevisiae -and ruthenium-catalyzed reactions in water (Zeror et al 2010) .…”

Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of ketones by biocatalysis using medlar (Mespilus germanicaL) fruit grown in Algeria

Bennamane

Zeror

Aribi‐Zouioueche

2014

Biocatalysis and Biotransformation

Self Cite

View full text Add to dashboard Cite

The biocatalytic reduction of ketones was performed using medlar fruit (Mespilus germanica L) , which is grown in large amounts in Algeria. Experiments were performed using aqueous medium with fresh medlar. Prochiral heteroaryl ketones containing furan, thiophene, chroman, and thiochroman moieties were reduced with enantiomeric excess (ee) of up to 98%. High enantioselectivities have been observed especially for the bioreduction of tetralone 4 and thiochromanone 5 with ee of 89% and 98%, respectively. Bioreduction using different parts of medlar indicate that chromanone 6 was reduced with good asymmetric inductions 77% Ͻ ee Ͻ 85% whichever part of fruit was employed (whole, fl esh, or juice) and medlar juice exhibited the best activity.Biocatal Biotransformation Downloaded from informahealthcare.com by Monash University on 12/15/14For personal use only.

show abstract

Enantioselective ketoester reductions in water: a comparison between microorganism- and ruthenium-catalyzed reactions

Cited by 22 publications

References 53 publications

Kinetic and Scanning Transmission Electron Microscopy Investigations on a MCM-41 Supported Cluster Derived Enantioselective Ruthenium Nanocatalyst

Kinetic and Scanning Transmission Electron Microscopy Investigations on a MCM-41 Supported Cluster Derived Enantioselective Ruthenium Nanocatalyst

Asymmetric Reduction of Ketones by Biocatalysis Using Clementine Mandarin (Citrus reticulata) Fruit Grown in Annaba or by Ruthenium Catalysis for Access to Both Enantiomers

Asymmetric reduction of ketones by biocatalysis using medlar (Mespilus germanicaL) fruit grown in Algeria

Contact Info

Product

Resources

About