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Synfacts 2007(3): 0294-0294
DOI: 10.1055/s-2007-968247
DOI: 10.1055/s-2007-968247
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Hydroxylation of Oxindoles and β-Keto Esters Using DBFOX Ligand
T. Ishimaru, N. Shibata*, J. Nagai, S. Nakamura, T. Toru*, S. Kanemasa
Nagoya Institute of Technology and Kyushu University, Kasuga, Japan
Further Information
Publication History
Publication Date:
20 February 2007 (online)
Significance
The enantioselective synthesis of 3-aryl- and 3-alkyl-3-hydroxy-2-oxindoles is described. Oxidation with the racemic oxidant 1 gave the best results when employing Zn(II)-DBFOX as catalyst. 3-Aryl-substituted 2-oxindoles gave the highest ee values, while the 3-alkyl derivates gave ee values >80% with reasonable yields. Use of this oxidation system with Ni(II)-DBFOX succeeded in the asymmetric oxidation of β-keto esters.