Electronically promoted Payne rearrangement of 3-CF3-2,3-epoxyalcohols.
[reaction: see text] Smooth and selective Payne rearrangement was achieved for the above types of epoxyalcohols with a CF(3) group so as to form thermodynamically more stable alkoxides, where the strongly electron-withdrawing nature of this moiety played a significantly important role and was proved to overcome increased steric instability of epoxides from syn-E to anti-Z isomers.
Yamazaki
Takashi
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Department of Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. tyamazak@cc.tuat.ac.jp
Ichige
Tatsuro
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Kitazume
Tomoya
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