Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

Chen, Bi‐Shuang; Hanefeld, Ulf

doi:10.1016/j.molcatb.2012.09.015

Cited by 11 publications

(11 citation statements)

References 51 publications

(74 reference statements)

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“…The compounds rac-2a-c were obtained in 68, 80, and 10% isolated yields, respectively, after column chromatography purification. The spectroscopic data ( 1 H and 13 C NMR) of the racemic cyclic 3-hydroxy ketones 2a-c were in agreement with those reported in the literature (Chen and Hanefeld 2013a;Chen et al 2015;Karmee et al 2011b;Resch et al 2013). In the next step, rac-2a-c were further converted to the corresponding acetates via acylation.…”

Section: Substrate Preparationsupporting

confidence: 90%

“…9 0 m i n ) , ( R -3 c : 8.05 min; S -3 c : 8.75 min). Stereochemical assignment was investigated in previous reports (Chen and Hanefeld 2013a;Chen et al 2015).…”

Section: General Methodsmentioning

confidence: 99%

“…Organic solventtolerant enzymes applicable as catalysts for organic synthesis have attracted the attention of many researchers (Doukyu and Ogino 2010). For example, nine different isolated lipases were screened for the kinetic resolution of 2a with vinyl acetate as acyl donor and solvent as we reported previously (Chen and Hanefeld 2013a). However, few organic solvent-tolerant bacteria have been identified, and an insufficient number of solvent-stable lipases have been isolated to satisfy the diverse substrates used in organic chemistry.…”

Section: Bioresolutionmentioning

confidence: 99%

“…strains showed modest enantioselectivities toward rac-2b (E-value of 14-16) and high enantioselectivity toward rac-2c (E-value of 40-45) but a very low E-value of 2 for rac-2a. (Chen and Hanefeld 2013a). The kinetic resolution of rac-2b by a lipase-like enzyme purified from the pancreatic porcine lipase (PPL) gave an E-value of 32 (Karmee et al 2011b).…”

Section: Bioresolutionmentioning

confidence: 99%

“…The preparation of the ideal biocatalyst, as well as the reaction itself, should be simple and cheap. In our previous work (Chen and Hanefeld 2013a;Karmee et al 2011b), we screened nine different isolated lipases (CAL-A, CAL-B, CRL, PCL, Amano PSD-I, Pseudomonas stutzeri, Alcaligenes sp., PFL, and pancreatic porcine lipase (PPL)) from commercial sources for the kinetic resolutions of rac-3-hydroxycylopentanone 2a and rac-3-hydroxycyclohexanone 2b and obtained enantiomerically enriched (R)-2a in 21% yield and 83% ee, corresponding to an E-value (enantiomeric ratio) of Electronic supplementary material The online version of this article (doi:10.1007/s10126-017-9755-7) contains supplementary material, which is available to authorized users. 20, and (R)-2b in 30% yield and 91% ee, corresponding to an Evalue of 32, respectively.…”

Section: Introductionmentioning

confidence: 99%

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Organic Solvent-Tolerant Marine Microorganisms as Catalysts for Kinetic Resolution of Cyclic β-Hydroxy Ketones

et al. 2017

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Chiral cyclic β-hydroxy ketones represent key motifs in the production of natural products of biological interest. Although the molecules are structurally simple, they require cumbersome synthetic steps to get access to them and their synthesis remains a challenge in organic chemistry. In this report, we describe a straightforward approach to enantiomerically enriched (R)-and (S)-3-hydroxycyclopentanone 2a, (R)-and (S)-3-hydroxycyclohexanone 2b, and (R )-and (S )-3-hydroxycycloheptanone 2c involving a transesterification resolution of the racemates using whole cells of marine microorganisms as catalysts and vinyl acetate the acyl donor and solvent. Twenty-six strains from a wide collection of isolates from marine sediments were screened, and seven strains were found to markedly catalyze the resolution in an asymmetric fashion. Using the strain Serratia sp., (R)-2a was isolated in 27% yield with 92% ee and (S)-2a in 65% yield with 43% ee, corresponding to an Evalue of 37; (R)-2b was isolated in 25% yield with 91% ee and (S)-2b in 67% yield with 39% ee, corresponding to an E-value of 40; and (R)-2c was isolated in 30% yield with 96% ee and (S)-2c in 63% yield with 63% ee, corresponding to an E-value of 75.

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Section: Substrate Preparationsupporting

confidence: 90%

“…9 0 m i n ) , ( R -3 c : 8.05 min; S -3 c : 8.75 min). Stereochemical assignment was investigated in previous reports (Chen and Hanefeld 2013a;Chen et al 2015).…”

Section: General Methodsmentioning

confidence: 99%

Section: Bioresolutionmentioning

confidence: 99%

Section: Bioresolutionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Organic Solvent-Tolerant Marine Microorganisms as Catalysts for Kinetic Resolution of Cyclic β-Hydroxy Ketones

et al. 2017

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Enantioselective Michael Addition of Water

Chen

Resch

Otten

et al. 2014

Chemistry A European J

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The enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important β-hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method. Deuterium labeling studies demonstrate that a Michael hydratase catalyzes the water addition exclusively with anti-stereochemistry.

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Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

et al. 2014

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A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated electronic circular dichroism [ECD] and vibrational circular dichroism [VCD] spectra) to determine the absolute configuration of both stereogenic centers in 4-hydroxy-5-methylcyclopent-2-en-1-one was demonstrated. It was also demonstrated that the concurrent application of ECD and VCD spectroscopy can be used for the determination of the configuration of two stereogenic centers.

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Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

Cited by 11 publications

References 51 publications

Organic Solvent-Tolerant Marine Microorganisms as Catalysts for Kinetic Resolution of Cyclic β-Hydroxy Ketones

Organic Solvent-Tolerant Marine Microorganisms as Catalysts for Kinetic Resolution of Cyclic β-Hydroxy Ketones

Enantioselective Michael Addition of Water

Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

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