René Faure, C. Felix, A. Laurent
Dec 15, 1997
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Journal
Acta Crystallographica Section C-crystal Structure Communications
Abstract
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, C17H14F3N04, (5), was obtained by a benzoylation reaction of the major diastereoisomer of (4). The three-(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 note-worthy that the presence of the CF 3 group enhances the diastereoselectivity of the reduction reaction.