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-fluoro­cyclo­propyl)­sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopropylidene compo...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 13; pp. 2280 - 2284
Main Authors Melngaile, Renate, Videja, Melita, Kuka, Janis, Kinens, Artis, Zacs, Dzintars, Veliks, Janis
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.04.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANALOGS
JULIA
METHYLENECYCLOPROPANE
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00579