Selectivity of Candida rugosa lipase in simultaneous separation of skeletal isomers, desymmetrization, and kinetic racemate cleavage of 9-oxabicyclononanediols

The diols 2 and 3, available in one step from cycloocta-1,5-diene, are selectively acetylated at the (R)-centers using Candida rugosa lipase to give the corresponding enantiopure compounds. In contrast, the (S,S)-enantiomer of 11 is transformed under identical conditions. The stereoselectivity of the lipase has been investigated by modeling of the transition state geometries at the active site of the enzyme.