3-chloro-benzenecarboperoxoic acid in dichloromethane 48 h; Ambient temperature;

dihydrogen peroxide; trifluoroacetic acid in dichloromethane T=0°C;

triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran; toluene T=-78°C; Mitsunobu reaction; 1 h;

Celite; sodium acetate; pyridinium chlorochromate in dichloromethane 1 h; Ambient temperature;

1: BF3*OEt2 / CH2Cl2 / -20 °C 2: aq. CaCO3, MeI / acetonitrile / 60 °C 3: BH3*Me2S / tetrahydrofuran / 0 °C 4: 1.) N-(phenylseleno)phthalimide, PBu3, 2.) Bu3SnH, AIBN / 1.) CH2Cl2, -20 deg C, 2.) PhMe, 80 deg C 5: 61 percent / PPh3, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature 6: MCPBA / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: 1.) N-(phenylseleno)phthalimide, PBu3, 2.) Bu3SnH, AIBN / 1.) CH2Cl2, -20 deg C, 2.) PhMe, 80 deg C 2: 61 percent / PPh3, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature 3: MCPBA / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: aq. CaCO3, MeI / acetonitrile / 60 °C 2: BH3*Me2S / tetrahydrofuran / 0 °C 3: 1.) N-(phenylseleno)phthalimide, PBu3, 2.) Bu3SnH, AIBN / 1.) CH2Cl2, -20 deg C, 2.) PhMe, 80 deg C 4: 61 percent / PPh3, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature 5: MCPBA / CH2Cl2 / 96 h / Ambient temperature View Scheme

1: 41 percent / 3 Angstroem molecular sieves, Ti(OiPr)4, CaH2, L-(+)-DIPT, tert-butyl hydroperoxide / CH2Cl2 / 12 h / -20 °C 2: 66 percent / sodium acetate, N-bromosuccinimide / tetrahydrofuran; H2O / 0.5 h / 0 °C 3: 60 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h / Ambient temperature 4: 90 percent / CeCl3*7H2O, NaBH4 / methanol / 0.17 h / 0 °C 5: 87 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 5 h / Ambient temperature 6: 100 percent / potassium carbonate / methanol / 2 h / Ambient temperature 7: 100 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 1 h / 0 °C 8: 96 percent / acetic acid, water / tetrahydrofuran / 24 h / Ambient temperature 9: 91 percent / PCC, sodium acetate, Celite / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 60 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h / Ambient temperature 2: 90 percent / CeCl3*7H2O, NaBH4 / methanol / 0.17 h / 0 °C 3: 87 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 5 h / Ambient temperature 4: 100 percent / potassium carbonate / methanol / 2 h / Ambient temperature 5: 100 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 1 h / 0 °C 6: 96 percent / acetic acid, water / tetrahydrofuran / 24 h / Ambient temperature 7: 91 percent / PCC, sodium acetate, Celite / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 66 percent / sodium acetate, N-bromosuccinimide / tetrahydrofuran; H2O / 0.5 h / 0 °C 2: 60 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h / Ambient temperature 3: 90 percent / CeCl3*7H2O, NaBH4 / methanol / 0.17 h / 0 °C 4: 87 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 5 h / Ambient temperature 5: 100 percent / potassium carbonate / methanol / 2 h / Ambient temperature 6: 100 percent / 4-dimethylaminopyridine, pyridine / CH2Cl2 / 1 h / 0 °C 7: 96 percent / acetic acid, water / tetrahydrofuran / 24 h / Ambient temperature 8: 91 percent / PCC, sodium acetate, Celite / CH2Cl2 / 1 h / Ambient temperature View Scheme