Chemo-enzymatic synthesis of spiro type gem-difluorocyclopropane as core molecule candidate for liquid crystal compounds

The synthesis of a novel spiro type gem-difluorocyclopropane building block, 1,1,7,7-tetrafluoro-2,8-bis(hydroxymethyl)dispiro[2.2.2.2]decane (1), has been accomplished in optically pure form using chemo-enzymatic reaction protocol. Various types of diesters or dialkyl ether were prepared from diol (+)-1 or (−)-1 in optically active form and their helical twisting power (HTP) was evaluated by addition of 1.0 wt% to a non-chiral nematic liquid crystal host. Although their HTP values were not significant, all compounds showed liquid crystal property with SmC* phase when they were dissolved (20 wt%) in achiral nematic host liquid crystal.