Synthetic Access to Fluorocyclopropylidenes
Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia- Kocienski olefination using the newly developed reagent 5-((2-fluorocyclo-propyl)sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopro-pylidene compo...
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| Vydané v: | Organic letters Ročník 25; číslo 13; s. 2280 - 2284 |
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| Hlavní autori: | , , , , , |
| Médium: | Journal Article |
| Jazyk: | English |
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Amer Chemical Soc
07.04.2023
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| Abstract | Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia- Kocienski olefination using the newly developed reagent 5-((2-fluorocyclo-propyl)sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopro-pylidene compounds includes hydrogenation to deliver fluorocyclopropylmethyl compounds and fluorinated cyclobutanones. The utility of the described method is demonstrated by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning biological properties of drug molecules. |
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| AbstractList | Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia-Kocienski olefination using the newly developed reagent 5-((2-fluorocyclopropyl)sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopropylidene compounds includes hydrogenation to deliver fluorocyclopropylmethyl compounds and fluorinated cyclobutanones. The utility of the described method is demonstrated by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning biological properties of drug molecules.Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia-Kocienski olefination using the newly developed reagent 5-((2-fluorocyclopropyl)sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopropylidene compounds includes hydrogenation to deliver fluorocyclopropylmethyl compounds and fluorinated cyclobutanones. The utility of the described method is demonstrated by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning biological properties of drug molecules. Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia- Kocienski olefination using the newly developed reagent 5-((2-fluorocyclo-propyl)sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopro-pylidene compounds includes hydrogenation to deliver fluorocyclopropylmethyl compounds and fluorinated cyclobutanones. The utility of the described method is demonstrated by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning biological properties of drug molecules. Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia-Kocienski olefination using the newly developed reagent 5-((2-fluorocyclopropyl)sulfonyl)-1-phenyl-1 -tetrazole. Derivatization of monofluorocyclopropylidene compounds includes hydrogenation to deliver fluorocyclopropylmethyl compounds and fluorinated cyclobutanones. The utility of the described method is demonstrated by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning biological properties of drug molecules. |
| Author | Zacs, Dzintars Melngaile, Renate Kinens, Artis Veliks, Janis Videja, Melita Kuka, Janis |
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| Title | Synthetic Access to Fluorocyclopropylidenes |
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