ChemInform Abstract: Enantioselective Synthesis of (R)‐(‐)‐1‐Phenylethanolamines Using Baker′s Yeast Reduction of Some α‐Substituted Methyl Phenyl Ketones.

Brenelli, E. C. S.; Carvalho, Marcia; Okubo, Masao; Marques, Maria Risoleta Freire; Moran, Paulo J. S.; Rodrigues, J. Augusto R.; Sorrilha, A. E. P. M.

doi:10.1002/chin.199313161

Cited by 4 publications

(3 citation statements)

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“…In 1987 [23], the baker's yeast reduction of 3-methyl-3-nitro-2-butanone to the (S)-enantiomer of corresponding alcohol (enantiomeric excess = ee > 96%) in 57% yield was described. A few years later, Moran et al [24] investigated the reduction of -nitroacetophenone (3a. R = Ph) in fermenting baker's yeast.…”

Section: Synthesis Of Nitroketones 3 and Biocatalysed Reduction To Dementioning

confidence: 99%

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

et al. 2018

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Chiral β-nitroalcohols are important building blocks in organic chemistry. The synthetic approach that is based on the enzyme-mediated reduction of α-nitroketones has been scarcely considered. In this work, the use of commercial alcohol dehydrogenases (ADHs) for the reduction of aromatic and aliphatic nitroketones is investigated. High conversions and enantioselectivities can be achieved with two specific ADHs, affording either the (S) or (R)-enantiomer of the corresponding nitroalcohols. The reaction conditions are carefully tuned to preserve the stability of the reduced product, and to avoid the hydrolytic degradation of the starting substrate. The further manipulation of the enantioenriched nitroalcohols into Boc-protected amminoalcohols is also described.

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Section: Synthesis Of Nitroketones 3 and Biocatalysed Reduction To Dementioning

confidence: 99%

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

et al. 2018

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“…An interesting chemoenzymatic synthetic route to obtain optically active 1-aryl-2-ethanolamines is from the enantioselective reduction of the correspondent α -haloacetophenones giving halohydrins that are transformed into an epoxy that reacts with the appropriate amine ( Scheme 1 ) [ 1 , 2 ].…”

Section: Introductionmentioning

confidence: 99%

Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

2011

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Enantioselective reductions of p-R1-C6H4C(O)CH2R2 (R1 = Cl, Br, CH3, OCH3, NO2 and R2 = Br, Cl) mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182 afforded the corresponding halohydrins with complementary R and S configurations, respectively, in excellent yield and enantiomeric excesses. The obtained (R)- or (S)-halohydrins are important building blocks in chemical and pharmaceutical industries.

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“…7–9 For example, there are a few reports that the reduction of benzoyl-formamide, one of the aromatic α-keto amides, with Saccharomyces cerevisiae gave to the corresponding ( R )-mandelamide in 60%–70% yield. 10,11 Furthermore, yeast and fungi such as Candida, Pichia , and Geotrichum species have a reducing activity toward 2-chlorobenzoylfomamide to the corresponding ( R )-hydroxy amide. 12,13 However, little information is known about the reduction of α-keto amide with other microorganisms.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Chiral 2-chloromandelamide: Stereoselective Reduction of an Aromatic α-keto Amide with Actinomycete Strains

et al. 2010

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Abstract:The stereoselective reduction of an aromatic α-keto amide with actinomycete strains was investigated. It was found that 2-chlorobenzoylformamide was reduced to the corresponding 2-chloromandelamide by mesophilic and thermophilic strains of actinomycetes. Among the strains tested, the reduction of 2-chlorobenzoylformamide by Streptomyces thermocyaneoviolaceus (one of thermophilic strains) in the presence of glycerol as an additive produced only (S)-2-chloromandelamide in 99% conversion with 99% enantiomeric excess (e.e.). On the other hand, the reduction by Streptomyces thermocarboxydovorans NBRC16324 at 45 °C or Thermoactinomyces vulgaris NBRC15851 cultivated in a soluble starch-based medium gave the corresponding (R)-hydroxy amide (conversion, 99%; 99% e.e.). Mesophilic and other thermophilic actinomycete strains also catalyzed the reduction to the corresponding (R)-hydroxy amide with 85%-99% e.e. Thus, the syntheses of both enantiomers of 2-chloromandelamide was achieved though the reduction of 2-chlorobenzoylformamide with different actinomycete strains.

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ChemInform Abstract: Enantioselective Synthesis of (R)‐(‐)‐1‐Phenylethanolamines Using Baker′s Yeast Reduction of Some α‐Substituted Methyl Phenyl Ketones.

Cited by 4 publications

References 0 publications

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

Biocatalytic Approach to Chiral β-Nitroalcohols by Enantioselective Alcohol Dehydrogenase-Mediated Reduction of α-Nitroketones

Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

Preparation of Chiral 2-chloromandelamide: Stereoselective Reduction of an Aromatic α-keto Amide with Actinomycete Strains

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