CyclopropyI building blocks for organic synthesis, 60 Synthesis and properties of optically active dispiro[2.0.2.1]heptane derivatives as novel ferroelectric liquid crystalline compounds

Enantioselective enzymatic acylation, using Lipase PS(R) (Pseudomonas sp., immobilized on Celite, Amano Pharmaceutical Co., Ltd.), of endo-dihalosubst ituted and nonsubstituted dispiro[2.0.2.1]heptylmethanol and endo-4-methyle ne-spiropentylmethanol provided the corresponding optically active compound s in high enantiomeric excesses (> 95% ee). Difluorocarbene addition onto t he optically active endo-4-methylenespiropentylmethanol yielded the first e nantiomerically pure difluorodispiro[2.0.2.1]heptylmethanols. The obtained optically active dispiro[2.0.2.1]heptane derivatives were used in syntheses of phenylpyrimidine derivatives, providing novel ferroelectric liquid crys talline compounds with unique physical properties.