A recyclable multi-substrates catalytic system for enantioselective reduction of ketones in water

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

doi:10.1016/j.molcata.2006.04.038

Cited by 40 publications

(18 citation statements)

References 35 publications

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“…We thus checked that under these conditions there was no decrease of the enantiomeric excesses compared to those observed with each single ketone. [10] The results are collected in Table 1 (entry 1). Surprisingly we observed a small increase in the asymmetric inductions when the mixture of ketones was reduced.…”

Section: Resultsmentioning

confidence: 99%

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Evaluation of Ligands for Ketone Reduction by Asymmetric Hydride Transfer in Water by Multi‐Substrate Screening

et al. 2008

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Various ligands for the ruthenium-catalyzed enantioselective reduction of ketones in water have been investigated. Multi-substrate reactions have been carried out for the comparison of various proline amides and aminoalcohol ligands. Two sets of six aromatic ketones have been selected in order to evaluate the enantiomeric excesses of all the resulting alcohols by a single chromatographic analysis. The proline amide derivative prepared from (1R,2S)-cis-aminoindanol revealed as the best ligand for most of the ketones used in the multi-substrate reductions. This ligand has been employed for the enantioselective reduction of a variety of other aromatic ketones and in all cases the enantiomeric excesses were improved compared to those obtained with phenylprolineamide used in our previous work.

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Section: Resultsmentioning

confidence: 99%

“…After concentration the product was purified by thin layer chromatography with hexane/ethyl acetate mixtures and spectral data compared with literature. Enantiomeric excesses were determined as precedently described, [10] or as indicated below.…”

Section: General Procedures For Catalytic Reactionsmentioning

confidence: 99%

Evaluation of Ligands for Ketone Reduction by Asymmetric Hydride Transfer in Water by Multi‐Substrate Screening

et al. 2008

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“…The absolute confi guration of major enantiomer was assigned by comparison with our previous work (Zeror et al 2006(Zeror et al , 2008. The conditions for the analysis of all alcohols are reported below: (S)-(-)-chroman-4-ol 6a: HPLC (CHIRALCEL OJ-H, Isohexane/ i -PrOH: 90/10, fl ow 1.0 mL/ min): t S ϭ 6.35 min, t R ϭ 7.29 min (Zeror et al 2008) or HPLC (CHIRALCEL OJ-H, Isohexane/ i -PrOH: 90/10, fl ow 0.5 mL/min): t S ϭ 12.57 min, t R ϭ 14.20 min.…”

Section: Chiral Gc Analysis And/or Chiral Hplc Analysismentioning

confidence: 99%

“…Asymmetric transfer hydrogenation of ketones has recently emerged as an alternative method for the production of chiral alcohols due to easy workup and availability of the reductants (Noyori & Hashiguchi 1997;Noyori & Ohkuma 2001;Palmer & Wills 1999;Gladiali & Alberico 2006;Samee et al 2006;Ikariya et al 2006). In this area, we have studied asymmetric transfer hydrogenation (ATH) of aromatic ketones in water using ruthenium-based catalysts (Zeror et al 2006(Zeror et al , 2008Boukachabia et al 2011). In the course of our previous investigations, the comparison between enantioselective bio-and metal-catalyzed reactions has been examined.…”

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

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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.

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“…Excellent enantiomeric excesses were obtained for ketones 10, 14, 15, 17, and 18. Enantiomeric excesses were determined by Chiralcel OD-H column according to the methods described in the Supplemental File [26][27][28][29].…”

Section: Asymmetric Reduction Of Ketones Using Aziridinemethanolsmentioning

confidence: 99%

Asymmetric Borane Reduction of Prochiral Ketones Catalyzed by α,α-Disubstituted Aziridinemethanols

Guo

Zhu

et al. 2008

Catal Lett

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A series of novel a,a-disubstituted aziridinemethanols have been developed for the enantioselective reduction of ketones in refluxing tetrahydrofuran. The optically active secondary alcohol products were obtained in good enantiomeric excess (*96.8%) and excellent yields. The results showed that the substituent groups on the hydroxyl-bearing carbon of aziridinemethanols obviously affected the enantioselectivity.

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A recyclable multi-substrates catalytic system for enantioselective reduction of ketones in water

Cited by 40 publications

References 35 publications

Evaluation of Ligands for Ketone Reduction by Asymmetric Hydride Transfer in Water by Multi‐Substrate Screening

Evaluation of Ligands for Ketone Reduction by Asymmetric Hydride Transfer in Water by Multi‐Substrate Screening

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

Asymmetric Borane Reduction of Prochiral Ketones Catalyzed by α,α-Disubstituted Aziridinemethanols

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