Janis Veliks et al. has developed a synthetically useful 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.
The authors have demonstrated the utility of this method by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning the biological properties of drug molecules.
The new approach has been published in the journal Organic Letters (IF=6.07).
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Melngaile, R., Videja, M., Kuka, J., Kinens,A., Zacs, Dz., Veliks J.*
Synthetic Access to Fluorocyclopropylidenes.
Org. Lett. 2023, 25, 13, 2280–2284. DOI: 10.1021/acs.orglett.3c00579