Enantio- and regioselective reduction of α-diketones by baker's yeast

Nakamura, Kaoru; Kondo, Shinichi; Kawai, Yasushi; Hida, Kouichi; Kitano, Kazutada; Ohno, Atsuyoshi

doi:10.1016/0957-4166(96)00020-1

Cited by 59 publications

(22 citation statements)

References 21 publications

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“…Hydrogenation of (a,b-diketones) can be performed by homogeneous (Hayakawa et al 2000), heterogeneous (Augustine 1997) or enzymatic catalysis (Nakamura et al 1996). The reduction of 1,2-, 1,3-and 1,4-diketones can be performed by Clemmensen reduction (Di Vona et al 1990), zinc being used as the reducing agent in acid media.…”

Section: Introductionmentioning

confidence: 98%

“…a-Hydroxyketones are widely used as intermediates for other products because its dual functionality allows their use in several reactions (Hayakawa et al 2000). For example a-hydroxyketones can be transformed into vic-diols or a-aminoketones (Nakamura et al 1996). Vic-diol compounds can be used as solvents or intermediates for the synthesis of other products (Grafje et al 2012).…”

Section: Introductionmentioning

confidence: 99%

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Hydrogenation of diacetyl over composite-supported egg-shell noble metal catalysts

et al. 2017

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Two composite supports with a mixed inorganic-organic structure were synthesized: BTAl and UTAl. Hydrophilic-hydrophobic dual properties of the supports were suitable for preparing egg-shell-supported metal catalysts for selective hydrogenation reactions. The catalysts were characterized by ICP, XRD, OM, TEM, EPMA, XPS and TGA. Their mechanical resistance was assessed. Activity and selectivity were tested with the hydrogenation of 2,3-butanedione (diacetyl) to 3-hydroxy-2-butanoneacetoin (acetoin). The same order of increasing metal particle size was found for the two tested supports: Pt \ Ru \ Pd. The XPS analysis showed that the metal/composite catalysts reduced in H2 at 503 K had two kinds of active sites: reduced (Me°) and electron-deficient (Me ? ). It was rationalized that the hydrogen bond cleavage was performed on the Me°active sites, while reactant adsorption occurred on the Me ? sites. The differences in activity and selectivity between the composite catalysts were attributed to electronic effects on the different metals and to different adsorptive properties of the different polymers. The high selectivity to acetoin was attributed to the preferential adsorption of diacetyl as compared to the adsorption of acetoin. The BTAl catalysts were slightly more active and selective than the UTAl ones. This was attributed to electronic effects caused by remnant organic groups on the composite supports (urethane or biphenyl on UTAl or BTAl, respectively). Pd-BTAl was the most active and selective catalyst, a fact related to electronic effects of both palladium and the support.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Hydrogenation of diacetyl over composite-supported egg-shell noble metal catalysts

et al. 2017

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“…However, 2-hydroxy ketones can also be produced biocatalytically, for example, via the reduction of a-diketones by baker's yeast (Nakamura, 1996). The enzymatic kinetic resolution of 2-hydroxy ketones and derivatives also yield enantioenriched 2-hydroxy ketones, albeit often with the characteristic disadvantage of kinetic resolutions, that is, a maximum conversion of 50% and difficult product purification (Duh et al, 1993;Kazlauskas and Bornscheuer, 1998).…”

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confidence: 98%

The production of (R)‐2‐hydroxy‐1‐phenyl‐propan‐1‐one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor

Hildebrand

Kühl

Pohl

et al. 2006

Biotech & Bioengineering

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Benzaldehyde lyase (BAL; E.C. 4.1.2.38) from Pseudomonas fluorescens Biovar I catalyzes the reversible formation of benzoins from aromatic aldehydes, and, moreover, the coupling of aromatic with aliphatic aldehydes yielding derivatives of (R)-2-hydroxy-1-phenyl- propan-1-one (R)-HPPs), which are important chiral building blocks. In this paper, we report on the development of a reactor system that allows the selective production of substituted (R)-HPP-derivatives. The reaction systems yielding (R)-1-(3-chloro-phenyl)-2-hydroxy- propan-1-one, (R)-2-hydroxy-3-methoxy-1-(4-methoxy-phenyl)-propan-1-one, and (R)-2-hydroxy-3,3-dimethoxy-1-phenyl-propan-1-one were investigated. A kinetic model optimized by batch experiments was developed, for the description of both batch and continuously operated reactors. This model was used to describe the HPP production in a continuously operated enzyme membrane reactor. The reactor type used combines the advantages of high conversion and excellent selectivity with high space-time yields and total turnover numbers of up to ttn=43,000. Products were obtained in high yield on a gram scale.

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“…To date, many procedures have been developed to prepare α-oxygenated ketones, such as α-oxygenation of enolates, [1] epoxidation, [2] dihydroxylation, [3] aminoxylation [4] of preformed enol ethers, enolates and enamines, and reduction of diketones. [5] In the past decade, the application of hypervalent iodine(III) reagents in organic synthesis has attracted intense interest due to their intriguing oxidizing properties, low toxicity, mild reactivity, ease of handling and ready availability. [6] A number of reports have demonstrated the feasibility of iodobenzene diacetate-mediated alkene dioxygenation in the presence or absence of external catalysts [7,8] and α-oxygenation of ketones.…”

Section: Introductionmentioning

confidence: 99%

Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of α-Oxygenated Ketones from Terminal Aryl Alkynes

Ren¹,

Zhong²,

Guo³

et al. 2016

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A facile and efficient method for preparation of α-oxygenated ketones has been developed via the reaction of terminal aryl alkynes with various iodobenzene dicarboxylates. When bis(trifluoroacetoxy)iodobenzene (PIFA) was used, α-hydroxy ketones were obtained in high to excellent yields. The hypervalent iodine(III) reagents can function as an electrophile, transferrable O-nucleophile, and an excellent leaving group. The protocol represents a direct, atom-efficient and metal-free conversion of alkynes into α-oxygenated ketones under mild conditions.

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Enantio- and regioselective reduction of α-diketones by baker's yeast

Cited by 59 publications

References 21 publications

Hydrogenation of diacetyl over composite-supported egg-shell noble metal catalysts

Hydrogenation of diacetyl over composite-supported egg-shell noble metal catalysts

The production of (R)‐2‐hydroxy‐1‐phenyl‐propan‐1‐one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor

Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of α-Oxygenated Ketones from Terminal Aryl Alkynes

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Enantio- and regioselective reduction of α-diketones by baker's yeast

Cited by 59 publications

References 21 publications

Hydrogenation of diacetyl over composite-supported egg-shell noble metal catalysts

Hydrogenation of diacetyl over composite-supported egg-shell noble metal catalysts

The production of (R)‐2‐hydroxy‐1‐phenyl‐propan‐1‐one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor

Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of &alpha;-Oxygenated Ketones from Terminal Aryl Alkynes

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Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of α-Oxygenated Ketones from Terminal Aryl Alkynes