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The unexpected high diastereofacial selectivity in hydrogenation of endo-olefins bearing a CF 3 group by Pd/C under a hydrogen atmosphere was discussed on the basis of experimental results as well as semiempirical molecular orbital calculations.
4-(1,1-Difluoro-2-ethoxycarbonyl)methyl-γ-butyrolactone (1) was prepared from the Reformatsky-type reaction of n-butyl 3-formylpropanoate with ethyl bromodifluoroacetate in Zn-THF system, and compound (1) was converted to α-methylene-γ-butyrolactone derivatives with a difluoromethylene unit at γ-position.
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