Abnormal Ito-Saegusa oxidation of TIPS enol ether assisted by a hydroxy group on a side chain |
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Authors: | Shiharu HiraokaShinji Harada Atsushi Nishida |
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Institution: | Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263 8522, Japan |
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Abstract: | Although Ito-Saegusa oxidation gives defined α,β-unsaturated ketones from silyl enol ether of ketones controlled by the position of the sp2 carbon of the silyl enol ether, the formation of a regioisomeric product that was oxidized abnormally was observed. The structural requirements for the substrates, the conditions, and a plausible mechanism are presented. |
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Keywords: | Ito-Saegusa oxidation Palladium α β-Unsaturated ketone Silys enol ether |
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