Preparative scale enantioseparation of 1-cyclohexyl-1-phenylethyl hydroperoxide and 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide on a modified cellulose stationary phase

The analytical and preparative scale optical resolution of 1-cyclohexyl-1-phenylethyl hydroperoxide and 1,2,3,4-tetrahydro-1-napthyl hydroperoxide has been achieved by chiral HPLC on a cellulose tris(3,5-dimethylphenyl carbamate) stationary phase coated on silica gel. The method has been used to obtain several hundred milligrams of highly enriched enantiomers (%ee >98) which were characterized by [α]_D and circular dichroism spectra, respectively. Configurational assignments were achieved for 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide enantiomers. © 1995 Wiley-Liss, Inc.