titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; alpha,alpha-dimethylbenzyl hydroperoxide in dichloromethane T=-35°C; Sharpless epoxidation; 36 h; optical yield given as percent ee;

tert.-butylhydroperoxide; silica gel in dichloromethane; water; acetone

titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate in dichloromethane T=-25°C; 3 h; Yield given. Yields of byproduct given;

titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester in dichloromethane T=-26°C; 26 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

dihydrogen peroxide 5 h; chloroperoxidase from Caldaromyces fumago, citrate buffer pH=5.0; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: NaH / tetrahydrofuran / 2 h / 0 °C 2: AcOH / methanol / 6 h / 40 °C 3: imidazole / dimethylformamide / 10 h / Ambient temperature 4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 6: NaOCl / CH2Cl2 / 4 h / Ambient temperature 7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 9: 95 percent / tetrahydrofuran / 12 h / Ambient temperature 11: 1.) CuCN 12: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 13: CrO3, H+ 14: aq. HF / acetonitrile View Scheme

1: NaH / tetrahydrofuran / 2 h / 0 °C 2: AcOH / methanol / 6 h / 40 °C 3: imidazole / dimethylformamide / 10 h / Ambient temperature 4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 6: NaOCl / CH2Cl2 / 4 h / Ambient temperature 7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 9: 95 percent / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: NaH / tetrahydrofuran / 2 h / 0 °C 2: AcOH / methanol / 6 h / 40 °C 3: imidazole / dimethylformamide / 10 h / Ambient temperature 4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 6: NaOCl / CH2Cl2 / 4 h / Ambient temperature 7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 9: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 10: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 11: CrO3, H+ View Scheme

1: NaH / tetrahydrofuran / 2 h / 0 °C 2: AcOH / methanol / 6 h / 40 °C 3: imidazole / dimethylformamide / 10 h / Ambient temperature 4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 6: NaOCl / CH2Cl2 / 4 h / Ambient temperature 7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 9: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 10: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 11: CrO3, H+ 13: Bu4NF View Scheme