6533b7cffe1ef96bd1258cdd
RESEARCH PRODUCT
Nucleophilic benzoylation using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of α-hydroxyacids
Gonzalo BlayIsabel FernándezBelen MonjePilar FormentinRafael RuizJosé R. Pedrosubject
chemistry.chemical_classificationDecarboxylationArylOrganic ChemistryAlkylationBiochemistryMedicinal chemistryUmpolungchemistry.chemical_compoundchemistryNucleophileDrug DiscoveryOxidative decarboxylationAlkylCarbaniondescription
Abstract The synthesis of alkyl aryl ketones using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion is reported (Umpolung). The methodology involves alkylation of methyl mandelate, hydrolysis of the ester group and oxidative decarboxylation of the resulting α-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 and advantageous conditions. The procedure is also applied to methyl mandelates substituted on the aromatic ring.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-02-01 | Tetrahedron |