Synthesis of optically active vicinal fluorocyclopentanols and fluorocyclopentanamines by enzymatic deracemization

Kolodiazhna, Olga O.; Prysiazhnuk, Dmitry; Kolodiazhna, Anastasy O.; Kolodiazhnyi, Oleg I.

doi:10.24820/ark.5550190.p011.634

Cited by 4 publications

(8 citation statements)

References 21 publications

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“…In this case, completion of the reaction at 50% conversion resulted in acylation of only the (R)-enantiomer of the racemic mixture. 17 As a result, unreacted (S)-2,3-dihydro-1H-inden-1-ol and (R)-2,3-dihydro-1H-inden-1-yl acetate were obtained in high chemical yield and high enantiomeric excess (ee). Subsequent hydrolysis of (R)dihydroindenyl acetate gave dihydroindenol of (R)-configuration.…”

Section: Resultsmentioning

confidence: 99%

“…CALB= Novozyme 435 ® Thus, all samples of fluoro-, chloro-, bromo-2,3-dihydro-1H-inden-1-ols were resolved into (S)-and (R)enantiomers isolated in pure form and characterized by physicochemical methods. 17 Some compounds were synthesized by metal complex catalysis, although with a lower enantiomeric purity. 9 The racemic and enantiomerically pure (S)-and (R)-enantiomers were then subjected to chiral HPLC analysis.…”

Section: Oacmentioning

confidence: 99%

“…Some 1 Н, 13 С NMR spectra of compounds 3-16 are described in our previous publication 17 and also presented in the Supplementary part. The results of chiral chromatograms, HRMS and physico-chemical constants (m.p.)…”

Section: Author(s)mentioning

confidence: 99%

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Сonvergent method for the determination of the absolute configurations of 2,3-dihydro-1H-inden-1-ols

Prysiazhnuk¹,

Kolodiazhna²,

Kolodiazhnyi³

2022

Arkivoc

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Racemic 2,3-dihydro-1H-inden-1-ols were resolved into enantiomers using kinetically controlled esterification of dihydroindenols by vinyl acetate with biocatalysis with Burkholderia cepacia lipase. The absolute configuration of halodihydroindenol enantiomers was defined by a convergent method of chiral HPLC analysis in combination with enzymatic analysis as well as single crystal X-Ray diffraction. The combined use of these methods increases the reliability in determining the absolute configurations of the studied compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Oacmentioning

confidence: 99%

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Сonvergent method for the determination of the absolute configurations of 2,3-dihydro-1H-inden-1-ols

Prysiazhnuk¹,

Kolodiazhna²,

Kolodiazhnyi³

2022

Arkivoc

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“…trans-2-Fluorocycloalkanols 88 (n = 1, 2) were used to prepare other building blocks via the common functional group transformations, e. g. α-fluoroketones 89, [89][90][91] cis-2-fluorocycloalkanols 90, [89,91,92] cis-2-fluorocycloalkylamines 91, [89,93] or cis-2-fluorocycloalkylhydrazines 92 [94] (Scheme 31).…”

Section: Synthesis Of β-Fluorinated Cycloalkyl Building Blocksmentioning

confidence: 99%

Fluorinated Cycloalkyl Building Blocks for Drug Discovery

et al. 2022

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The review covers various aspects of fluorinated cycloalkyl (C3−C7) building blocks for drug discovery, including their synthesis, key physicochemical properties, and biological and medicinal applications of their derivatives. The discussed synthetic methods include classical nucleophilic fluorinations of various substrates, the addition of fluorine and another heteroatom to double bonds, cycloadditions and other transformations of fluorine‐containing substrates, as well as some newer reactions like fluorination of non‐activated and remotely activated C−H bonds, decarboxylative and deborylative fluorinations, etc. The known data on the effect of introducing the fluorinated cycloalkyl groups on the compound's key in vitro parameters (such as acidity/basicity, lipophilicity, conformational behavior, and short contact capabilities) are surveyed. Finally, applications of fluorinated cycloalkyl building block derivatives in the design of biologically active compounds (including marketed drugs Maraviroc, Ivosidenib, and Sitafloxacin) are covered, with a focus on the fluorination impact.

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“…таблицю). С ЯМР спектри сполук 3-16 описані в раніше опублікованій нами роботі [6], спектри сполук 17-20 -у статті [16]. Результати ВЕРХ, GR-MS зведені в таблиці.…”

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Визначення Абсолютної Конфігурації Дигідроінденолів Методами Ферментативного Аналізу Та Хіральної ВЕРХ

Присяжнюк¹,

Kolodiazhna²,

Kolodiazhna³

et al. 2022

Dopov. Nac. akad. nauk Ukr.

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Рацемічні 1,2-дигідроінденоли розділено на енантіомери за допомогою кінетичної контрольованої естерифікації в присутності біокаталізатора Burkholderia cepacia lipase (BCL). Досліджено також ферментативне розділення ацетатів галогендигідроінденолів гідролізом у присутності іммобілізованої на діатомітних ліпазах Candida antarctica B. Для визначення абсолютної конфігурації стереоізомерів галогендигідроінденолів використовували хіральний ВЕРХ-аналіз у поєднанні з ферментативною кінетичною дерацемізацією із застосуванням правила Казлаускаса, а також рентгеноструктурного аналізу для деяких сполук. Сумісне використання декількох методів підвищує надійність у визначенні абсолютної конфігурації досліджуваних сполук.

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Synthesis of optically active vicinal fluorocyclopentanols and fluorocyclopentanamines by enzymatic deracemization

Cited by 4 publications

References 21 publications

Сonvergent method for the determination of the absolute configurations of 2,3-dihydro-1H-inden-1-ols

Сonvergent method for the determination of the absolute configurations of 2,3-dihydro-1H-inden-1-ols

Fluorinated Cycloalkyl Building Blocks for Drug Discovery

Визначення Абсолютної Конфігурації Дигідроінденолів Методами Ферментативного Аналізу Та Хіральної ВЕРХ

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