K. Sakaguchi et al., PD-C ASSISTED SYNTHESIS OF CIS-2,4-DISUBSTITUTED GAMMA-BUTYROLACTONESAND THEIR PROPERTIES FOR FERROELECTRIC LIQUID-CRYSTALS, Synlett, (5), 1997, pp. 624
Cis isomers of optically active 2,4-disubstituted gamma-butyrolactone,
1 - 4, as chiral dopants for ferroelectric Liquid crystals (FLCs) are
synthesized in a stereoselective manner via a Pd-C catalyzed hydrogen
ation of the endo CC double bond isomers of (4R)-2,4-disubstituted gam
ma-butyrolactone, 23, 19, 20, and 21, respectively. The synthesis invo
lved a novel exo to endo isomerization of the CC double bond effected
by Pd-C in the absence of hydrogen.