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A magnesium enamide derived from N-2-(N',N'-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an alpha-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.
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Hatakeyama et al. (2005) studied this question.
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