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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Bibliographic Details
Published in:Organic 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
Language:English
Published: WASHINGTON Amer Chemical Soc 07.04.2023
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANALOGS
JULIA
METHYLENECYCLOPROPANE
ISSN:1523-7060, 1523-7052, 1523-7052
Online Access:Get more information
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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-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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c00579