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. (C) 2009 Elsevier B.V. All rights reserved.