Abstract
Abstract The reagent formed by the reaction of diethyl azodicarboxylate (1) and triphenylphosphine (2) reacted with alcohols and ethyl cyanoacetate (6) to give alkylated products in 30–80% yields. When ethyl acetoacetate, 1,3-cyclopentanedione, or 1,3-cyclohexanedione was used in place of 6, the corresponding O-alkylated products were obtained. The reaction of either (S)-(−)-ethyl lactate or (S)-(−)-ethyl 2-hydroxy-3-phenylpropionate with 1, 2, and 6, followed by hydrolysis resulted in the formation of (S)-(−)-methylsuccinic acid or (S)-(−)-benzylsuccinic acid. The results indicate that nearly complete inversion of the configuration takes place in the alkylation step.
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