Tetrahedron

Nucleophilic benzoylation using lithiated methyl mandelate as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of α-hydroxyacids

…, I Fernández, P Formentin, B Monje, JR Pedro, R Ruiz

Index: Blay, Gonzalo; Fernandez, Isabel; Formentin, Pilar; Monje, Belen; Pedro, Jose R; Ruiz, Rafael Tetrahedron, 2001 , vol. 57, # 6 p. 1075 - 1081

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Citation Number: 21

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 ...

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