6533b7d3fe1ef96bd12600f9

RESEARCH PRODUCT

A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes

Attila Márió RemeteSantos FusteroLoránd KissMelinda NonnFerenc Fülöp

subject

Hydrocarbons FluorinatedPharmaceutical ScienceEpoxideAlkenesstereoselectivity010402 general chemistry01 natural sciencesArticleAnalytical Chemistrylcsh:QD241-441Fluorideschemistry.chemical_compoundlcsh:Organic chemistryDrug DiscoveryOrganic chemistryPhysical and Theoretical Chemistryamino acidsSulfur Compoundsoxirane; fluorination; amino acids; stereoselectivity; regioselectivity010405 organic chemistryOrganic ChemistryRegioselectivityStereoisomerismfluorination0104 chemical sciencesCycloalkanechemistryChemistry (miscellaneous)oxiraneregioselectivityReagentEpoxy CompoundsMolecular MedicineStereoselectivityFluoride

description

A novel selective and substrate-dependent synthetic protocol has been developed towards the synthesis of various fluorine-containing, highly functionalized cycloalkane derivatives. The method involves the stereoselective epoxidation of some unsaturated cyclic beta-amino acid derivatives as model compounds, followed by a regioselective fluoride opening of oxiranes under various conditions with Deoxofluor and XtalFluor-E reagents, thereby offering an insight into this new epoxide opening methodology with fluoride.

yearjournalcountryeditionlanguage
2016-11-17Molecules
https://doi.org/10.3390/molecules21111493