Enantioselective fluorination of β-keto ester using a PEG-bound urea-containing chiral quaternary ammonium salt catalyst

Zhang, Baohua; Shi, Lei; Guo, Ruixia; Liu, Sijie

doi:10.3998/ark.5550190.p009.420

Cited by 11 publications

(14 citation statements)

References 8 publications

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“…Therefore, this immobilization approach is attractive from the viewpoint of green chemistry. [111] Asymmetric phase-transfer fluorinations of simple carboxylic acid derivatives are uncommon. Transformation of 3-substituted benzofuran-2(3H)-ones [50 % K 2 HPO 4 (aq)/PhMe biphasic system, NFSI, chiral quaternary phosphonium salt catalyst, 25 °C, 12 h] proceeded with excellent yields but up to 56 % ees.…”

Section: Fluorination Of β-Keto Esters and Related Compoundsmentioning

confidence: 99%

“…Practically, all reported fluorinations of β‐keto esters under chiral phase‐transfer conditions utilized quaternary ammonium salt catalysts. Mainly cyclic (conformationally restricted) β‐keto esters were fluorinated successfully under these conditions [106–111] …”

Section: Asymmetric C−f Bond‐forming Reactions Using Chiral Phase‐transfer Catalysismentioning

confidence: 99%

“…The recovered catalyst was reused six times without deterioration of either the yield or the enantioselectivity. Therefore, this immobilization approach is attractive from the viewpoint of green chemistry [111] …”

Section: Asymmetric C−f Bond‐forming Reactions Using Chiral Phase‐transfer Catalysismentioning

confidence: 99%

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Asymmetric Methods for Carbon‐Fluorine Bond Formation

et al. 2021

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In memory of Ferenc FülöpAs a consequence of the ever-increasing relevance of fluorinated drugs in medicinal chemistry, organofluorine chemistry has become a hot topic research area during the last decade. Asymmetric carbon-fluorine bond-forming reactions have enormously developed in recent years with considerable findings related to novel reactions and synthetic approaches. These new synthetic efforts have contributed to the access to a growing number of fluorinated molecules and complex natural or synthetic products of high relevance in medicinal chemistry and drug research. Illustrative examples of novel synthetic methodologies, including organocatalytic processes, asymmetric syntheses or phase-transfer catalytic methods for the enantioselective incorporation of fluorine atom(s) into versatile molecular entities, are covered in the current Review, focusing on main contributions of the last ten years.

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Section: Fluorination Of β-Keto Esters and Related Compoundsmentioning

confidence: 99%

Section: Asymmetric C−f Bond‐forming Reactions Using Chiral Phase‐transfer Catalysismentioning

confidence: 99%

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Asymmetric Methods for Carbon‐Fluorine Bond Formation

et al. 2021

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“…Based on the previous report, [60] Shi and coworkers developed in 2016 a new protocol in which they were able to support a similar catalyst 59 on polyethylene glycol (PEG) [61] . This approach makes it easy to recover the catalyst by precipitation in diethyl ether, [62] still being able to operate in homogeneous conditions.…”

Section: (Thio)urea Derivatives As Organocatalysts For Asymmetric Flumentioning

confidence: 99%

“…This catalyst was also used to carry out the enantioselective fluorination of β‐ketoesters 33–36 (Scheme 20). [61] …”

Section: (Thio)urea Derivatives As Organocatalysts For Asymmetric Flumentioning

confidence: 99%

Asymmetric Fluorination Reactions promoted by Chiral Hydrogen Bonding‐based Organocatalysts

et al. 2020

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Fluorinated compounds can exhibit interesting biological properties. The importance of these species has made that the chemistry of fluorine has experienced a great development. On this review, the recent advances on asymmetric fluorination reactions promoted by chiral hydrogen bonding-based organocatalysts are discussed. Hence, examples using phosphoric acid, carboxylic acid, (thio)urea and squaramide derivatives are illustrated. The growth of this field is amazing. We have only considered pivotal works in which direct fluorination takes place using a fluorinating agent, leaving aside the reactions where a fluorine atom is incorporated from the beginning as part of other reactants. Herein, the scarce existing examples on this field of research have been compiled.

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