α-fluorination of ketones by xenon and iodobenzene difluorides: A stereochemical evidence demonstrating their mechanistic differences |
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Authors: | Tadahiko Tsushima Kenji Kawada Teruji Tsuji |
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Institution: | Shionogi Research Laboratories, Shionogi & Co., Ltd. Fukushima-ku, Osaka, 553 Japan |
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Abstract: | Xenon difluoride reacts smootlhy with various steroid silyl enol ethers in the absence of any acid catalyst to afford stereoselectively α-oriented α-fluoroketones in good yields while iodotoluene difluoride reacts rather sluggishly with these silyl enol ethers to competitively produce β-oriented α-fluoro ketones, elimination and other nucleophilic substitution products. The observed stereochemical contrast clearly suggests an electrophilic and nucleophilic mechanism for these reactions, respectively. |
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