Asymmetric synthesis of 5,6-dehydrosenedigitalene using lipase-catalyzed highly enantioselective transesterification of a primary alcohol with vinyl 3-(4-trifluoromethylphenyl)propanoate

The highly enantioselective kinetic resolution of a racemic primary alcohol by lipase-catalyzed transesterification with vinyl 3-(4-trifluoromethylphenyl)propanoate afforded an enantiomerically pure primary alcohol. The versatility of this approach is shown in the asymmetric synthesis of 5,6-dehydrosenedigitalene (R)-1.

Figure optionsDownload as PowerPoint slide

(R)-6-(4-Methylphenyl)-1-hepteneC14H20Ee = >99%[α]D23=-21.6 (c 1.2, CHCl3)Source of chirality: lipase-catalyzed resolutionAbsolute configuration: R

(R)-2-(4-Methylphenyl)-6-heptene-l-olC14H20OEe = >99%[α]D24=-12.6 (c 0.8, CHCl3)Source of chirality: lipase-catalyzed resolutionAbsolute configuration: R

(S)-6-(4-Methylphenyl)-1-hepteneC14H20Ee = >99%[α]D24=+23.0 (c 1.1, CHCl3)Source of chirality: lipase-catalyzed resolutionAbsolute configuration: S

(S)-2-(4-Methylphenyl)-6-heptene-1-olC14H20OEe = >99%[α]D24=+16.0 (c 1.1, CHCl3)Source of chirality: lipase-catalyzed resolutionAbsolute configuration: S