Preparative scale enantioseparation of 1‐cyclohexyl‐1‐phenylethyl hydroperoxide and 1,2,3,4‐tetrahydro‐1‐naphthyl hydroperoxide on a modified cellulose stationary phase
- 1 January 1995
- Vol. 7 (4) , 243-247
- https://doi.org/10.1002/chir.530070410
Abstract
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.Keywords
This publication has 16 references indexed in Scilit:
- Kinetic resolution of chiral hydroperoxidesvia Sharpless EpoxidationAdvanced Synthesis & Catalysis, 1994
- Enzym‐katalysierte asymmetrische Synthese: Die kinetische Racematspaltung von chiralen Hydroperoxiden durch enantioselektive Reduktion zu Alkoholen mit MeerrettichperoxidaseAngewandte Chemie, 1993
- Chloroperoxidase-catalyzed asymmetric synthesis: enantioselective reactions of chiral hydroperoxides with sulfides and bromohydroxylation of glycalsThe Journal of Organic Chemistry, 1992
- Kinetic resolution of 1-methyl-1-phenylpropyl hydroperoxide via Sharpless epoxidationTetrahedron: Asymmetry, 1992
- A new synthon for optically active diene hydroperoxidesThe Journal of Organic Chemistry, 1991
- Benzoyl cellulose beads in the pure polymeric form as a new powerful sorbent for the chromatographic resolution of racematesChirality, 1991
- Preparative, enzymic synthesis of linoleic acid (13S)-hydroperoxide using soybean lipoxygenase-1The Journal of Organic Chemistry, 1990
- Enzymatic resolution of racemic hydroperoxides in organic solvent.Agricultural and Biological Chemistry, 1988
- Asymmetric Oxidation of Sulfides with Optically Active Hydroperoxides Prepared by Singlet Oxygenation of Thiazolidine DerivativesBulletin of the Chemical Society of Japan, 1986
- Autoxydation von Kohlenwasserstoffen: Über ein durch Autoxydation erhaltenes Tetrahydro‐naphthalin‐peroxyd (I. Mitteil.)Berichte der deutschen chemischen Gesellschaft (A and B Series), 1933