1,1,1-Trifluoro-3-phenyl-2-butyl p-Nitrobenzoate

The reduction of the trifluoromethylated ketone, 1,1,1-trifluoro-3-phenyl-2-butanone, (1), or its hydrogenated homologue, 3-phenyl-2-butanone, (2), with lithium aluminium hydride (LAH) gave 1,1,1-trifluoro-3-phenyl-2-butanol, (4), or 3-phenyl-2-butanol, (3), respectively, as a mixture of the (R*R*)/(R*S*) isomers. The title compound, C₁₇H₁₄F₃NO₄, (5), was obtained by a benzoylation reaction of the major diastereoisomer of (4). The threo-(R*R*) configuration is clearly evidenced in the crystal structure of (5). So, in the reduction of (1) or (2), the threo isomer is the major product. It is noteworthy that the presence of the CF₃ group enhances the diastereoselectivity of the reduction reaction.

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