1472-01-1Relevant articles and documents
Enzymes in organic synthesis. 33. Stereoselective pig liver esterase-catalyzed hydrolyses of meso cyclopentyl-, tetrahydrofuranyl-, and tetrahydrothiophenyl-1,3-diesters
Jones, J. Bryan,Hinks, R. Scott,Hultin, Philip G.
, p. 452 - 456 (2007/10/02)
Preparative-scale pig liver esterase-catalyzed hydrolyses of five-membered ring meso-1,3-diesters are enantiotopically selective.While pro-S enantiotopic selectivity is exhibited in each case, the absolute configuration sense of the hydrolysis in the cyclopentyl series is opposite to that of both the tetrahydrofuranyl and tetrahydrothiophenyl diesters.The enantiomeric excess levels induced are in the 34-46percent range.
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
Nakazaki, Masao,Naemura, Koichiro,Makimura, Masaru,Matsuda, Atsushi,Kawano, Takaaki,Ohta, Yoshihiro
, p. 2429 - 2435 (2007/10/02)
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-C2h-trans,trans-10, and a mixture of meso-C2h-11 and meso-C2v-cis,cis crown ethers 12.Their selective transport of alkali metal cations is reported.