The Addition of Lithium Salts of O-Alkyloximes to Aldehydes: Synthesis of ß-Keto O-Alkyloximes
17 September 2002 (online)
Addition of lithium salts of oxime O-ethers to aldehydes affords the thermodynamically unfavored ß-hydroxy (Z)-O-alkyloximes. Oxidation of the hydroxy function with chromium trioxide/pyridine complex gives the ß-keto O-alkyloximes. Facile alkylation of the 1,3-dicarbonyl analogs is possible via their sodium or lithium salts.