Synthesis of Stereoisomeric Crown Ethers Composed of cis- and trans-2,5-Bis(hydroxymethyl)tetrahydrofuran Units and Their Selective Transport of Alkali Metal Cations through Liquid Membranes

Article abstract of DOI:10.1021/jo00133a038

Optical resolution of trans-tetrahydrofuran-2,5-dicarboxylic acid (13) was carried out via the (+)-2-(1-aminoethyl)naphthalene salt, and conversion of the (+) enantiomer 13 into (+)-2,5-dimethyltetrahydrofuran (17) of known configuration established its 2R,5R configuration.Condensation of (+)- and (-)-trans-ditosylates 15 and cis-ditosylate 20 with pyrocatechol afforded (-)-D₂-trans,trans-8, (-)-C₁-cis,trans-9, meso-C_2h-trans,trans-10, and a mixture of meso-C_2h-11 and meso-C_2v-cis,cis crown ethers 12.Their selective transport of alkali metal cations is reported.