New route to enantiomers of cyclic β-hydroxyethers. The crystal structure of (S)-(+)-tetrahydrofurfuryl-O,O′-diacetyl-(2R,3R)-hydrogentartrate

Title compounds 1-2 were readily resolved into their enantiomers by crystallizing their half esters formed with O,O'-diacetyl-(2R,3R)-tartaric acid. An intermolecular H-bond between the flee carboxyl group and the ring oxygen, determined by single crystal X-ray study of (S)-(+)-tetrahydrofurfuryl-O,O'-diacetyl-(2R,3R)-hydrogentartrate, enhances the selectivity and the crystallizing ability itself. Copyright (C) 1996 Elsevier Science Ltd