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 ® ( Pseudomonas sp., immobilized on Celite, Amano Pharmaceutical Co., Ltd.), of endo ‐dihalosubstituted and nonsubstituted dispiro[2.0.2.1]heptylmethanol and endo ‐4‐methylenespiropentylmethanol provided the corresponding optically active compounds in high enantiomeric excesses (> 95% ee ). Difluorocarbene addition onto the optically active endo ‐4‐methylenespiropentylmethanol yielded the first enantiomerically 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 crystalline compounds with unique physical properties.