Regioselective Fluorohydrin Synthesis from Allylsilanes and Evidence for a Silicon–Fluorine Gauche Effect
Alexie W. Clover,
Adam P. Jones,
Robert F. Berger
et al.
Abstract:Allylsilanes can be regioselectively transformed into the corresponding 3-silylfluorohydrin in good yield using a sequence of epoxidation followed by treatment with HF•Et 3 N with or without isolation of the intermediate epoxide. Various siliconsubstitutions are tolerated, resulting in a range of 2-fluoro-3-silylpropan-1-ol products from this method. Whereas other fluorohydrin syntheses by epoxide opening using HF•Et 3 N generally require more forcing conditions (e.g., higher reaction temperature), opening of … Show more
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