Pd-C Assisted Synthesis of cis-2,4-Disubstituted γ-Butyrolactones and their Properties for Ferroelectric Liquid Crystals

Kazuhiko Sakaguchi; Yasuo Kawamura; Sinichi Saito; Yasufumi Ohfune

doi:10.1055/s-1997-3233

Synlett 1997; 1997(5): 624-626
DOI: 10.1055/s-1997-3233

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Pd-C Assisted Synthesis of cis-2,4-Disubstituted γ-Butyrolactones and their Properties for Ferroelectric Liquid Crystals

Kazuhiko Sakaguchi¹ , Yasuo Kawamura, Sinichi Saito² , Yasufumi Ohfune¹

¹Department of Material Science, Faculty of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558, Japan
²Chisso Petrochemical co., Specialty Chemicals Research Center, Goikaigan 5-1, Ichihara, Chiba 290, Japan

Abstract

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Cis isomers of optically active 2,3-disubstituted γ-butyrolactone, 1 - 4, as chiral dopants for ferroelectric liquid crystals (FLCs) are synthesized in a stereoselective manner via a Pd-C catalyzed hydrogenation of the endo CC double bond isomers of (4R)-2,4-disubstituted γ-butyrolactone, 23, 19, 20, and 21, respectively. The synthesis involved a novel exo to endo isomerization of the CC double bond effected by Pd-C in the absence of hydrogen.

γ-butyrolactone - ferroelectric liquid crystal - isomerization - stereoselective hydrogenation - Pd-C

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