6533b86cfe1ef96bd12c8b85
RESEARCH PRODUCT
Nucleophilic benzoylation using a mandelic acid dioxolanone as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of α-hydroxyacids
Gonzalo BlayJosé R. PedroIsabel FernándezBelen Monjesubject
AlkylationDecarboxylationCarbonatesPharmaceutical ScienceAlkylationdioxolanoneArticlecatalystsAnalytical ChemistryUmpolunglcsh:QD241-441chemistry.chemical_compoundNucleophilelcsh:Organic chemistryDrug DiscoveryMoietyOrganic chemistryPhysical and Theoretical ChemistrydecarboxylationOxidative decarboxylationCarbanionMolecular StructureChemistryOrganic ChemistryDioxolanesBenzoic AcidKetonesMandelic acidcobaltChemistry (miscellaneous)Umpolung.Molecular MedicineMandelic AcidsHydroxy AcidsOxidation-Reductiondescription
The synthesis of alkyl aryl ketones using a mandelic acid dioxolanone as a synthetic equivalent (Umpolung) of the benzoyl carbanion is reported. The methodology involves alkylation of the mandelic acid dioxolanone, hydrolysis of the dioxolanone moiety in the alkylated products and oxidative decarboxylation of the resulting alpha-hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co (III) complex in the presence of pivalaldehyde under very mild conditions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-04-30 |