Stereoisomeric flavour compounds. LXIII. 4-Hydroxypentan-2-one enantiomers - Structure and properties

Article abstract of DOI:10.1016/S0957-4166(00)80172-X

From racemic 4-hydroxypentan-2-one and (S)-tetrahydro-5-oxo-2-furancarboxylic acid chloride the corresponding diastereomeric esters were generated, subsequently separated by liquid chromatography and hydrolyzed to yield pure enantiomers of 4-hydroxypentan-2-one. The X-ray crystal structures of the diastereomeric esters as well as the odour impression of the pure 1,3-ketol enantiomers are reported.