Collect. Czech. Chem. Commun.
1990, 55, 2685-2691
https://doi.org/10.1135/cccc19902685
Preparation of both enantiomers of (1R*, 2S*)-1-cyclohexyl-1,2-propanediol from the commercial Neuberg's ketol
Otakar Červinka and Vladimír Stružka
Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
Abstract
Both the optically pure enantiomers of (1R*, 2S*)-1-cyclohexyl-1,2-propanediol (II) were prepared from commercial (R)-(-)-1-phenyl-1-hydroxy-2-propanone (I; Neuberg's ketol). (1R, 2S)-(+)-1-Cyclohexyl-1,2-propanediol ((+)-II) was obtained in 19% total yield, its (1S, 2R)-enantiomer ((-)-II) in 8% yield. Both diols, as well as their precursors, enantiomeric (1R*, 2S*)-1-phenyl-1,2-propanediols (IIIa), are suitable chiral synthons.
