Preparation of both enantiomers of (1R*, 2S*)-1-cyclohexyl-1,2-propanediol from the commercial Neuberg's ketol

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.

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