Synthesis 1990; 1990(6): 502-504
DOI: 10.1055/s-1990-26920
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The Addition of Lithium Salts of O-Alkyloximes to Aldehydes: Synthesis of ß-Keto O-Alkyloximes

Shimon Shatzmiller* , Eliezer Bahar, Sorin Bercovici, Alexander Cohen, Gerhard Verdoorn
  • *The Beverly and Raymond Sackler Faculty of Exact Sciences, School of Chemistry, Tel-Aviv University, Ramat-Aviv, Tel-Aviv 69978, Israel
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Publication History

Publication Date:
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.