6533b7d4fe1ef96bd1261f4f
RESEARCH PRODUCT
Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids
Melinda NonnMatti HaukkaFerenc FülöpFerenc FülöpReijo SillanpääSantos FusteroLoránd Kisssubject
molecular diversitycyclizationDouble bondHalogenationHydrocarbons FluorinatedStereochemistryMolecular Conformationchemistry.chemical_elementCyclopentanes010402 general chemistryRing (chemistry)Crystallography X-Ray01 natural sciencesBiochemistrychemistry.chemical_compoundfluorineCyclopentaneta116Norbornenechemistry.chemical_classificationamino acidssubstituent effects010405 organic chemistryOrganic ChemistrySubstrate (chemistry)StereoisomerismGeneral Chemistry0104 chemical sciencesAmino acidchemistryFluorineOxidation-Reductiondescription
This work describes a substrate-directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH2 F or CHF2 moieties in their structure have been synthesized from diexo- or diendo-norbornene β-amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon-carbon double bond of the norbornene β-amino acids, followed by transformation of the resulted "all cis" and "trans" diformyl intermediates by fluorination with "chemodifferentiation".
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-10-10 | Chemistry: An Asian Journal |