Abstract
Previously reported syntheses of 3-functionalized silyl enol ethers using allyloxysilanes are hindered by undesirable reactions owing to retro Brook rearrangements. In this study, various 3-functionalized (Z)-silyl enol ethers were synthesized from readily available 1-arylallylic alcohols using (trimethylsilyl)methylpotassium as a base. C,O-Difunctionalization of the in situ-generated dipotassio α,β-dianion with electrophiles and silyl chlorides is key to the success of this transformation. Control experiments confirmed that the dianion has higher nucleophilicity and thermal stability than related siloxyallylpotassiums.
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