Biocatalytic-Based Synthesis of Optically Pure (C-6)-Functionalized 1-(tert-Butyldimethylsilyloxy) 2-Methyl-(E)-2-heptenes

Article abstract of DOI:10.1016/S0957-4166(00)86349-1

Controlled lipase hydrolysis of sulcatol chloroacetate at pH 7.2 to 55percent completion gives (R)-(-)-sulcatol of 89percent ee.Alkaline hydrolysis of the unreacted ester provides the (S)-(+) enantiomer efficiently and in an optically pure state.The latter is protected at its hydroxyl group, oxidized at its less sterically hindered terminal methyl group, and trans-formed into useful bifunctional reagents possessing 100percent ee.