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A series of 2-hydroxy-propionic acid ethyl ester derivatives was prepared in good yields by reaction of o- and p-nitrobenzyl chlorides (1, 8) with various α-carbonyl esters in presence of tetrakis(dimethylamino)ethylene (TDAE). This reaction was generalized to α-ketolactam and α-ketomalonate.
Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of chlorodifluoromethylated ketones1–3. The generated α,α-difluoroacetyl anion was trapped with several aldehydes4–7, under mild conditions, to give the corresponding 2,2-difluoro-3-hydroxy ketone derivatives8–13, in moderate yields.
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