acetyl chloride in tert-butyl methyl ether T=35 - 50°C;

acetyl chloride T=20 - 50°C; Product distribution / selectivity;

osmium(VIII) oxide; 4-methylmorpholine N-oxide in water; tert-butyl alcohol T=20°C; 16 h;

hydrogenchloride 18 h; Ambient temperature;

1.1: pyridine / 20 °C 2.1: 32percent HBr / 1,2-dichloro-ethane; acetic acid / 2 h / 0 °C 2.2: 6.22 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dichloro-ethane / 0.5 h / 20 °C 3.1: SnCl4 / CH2Cl2 / -18 °C 4.1: 88 percent / CeCl3*7H2O; NaBH4 / methanol / 0.33 h / 0 °C 5.1: 82 percent / OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 16 h / 20 °C View Scheme

1.1: 32percent HBr / 1,2-dichloro-ethane; acetic acid / 2 h / 0 °C 1.2: 6.22 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dichloro-ethane / 0.5 h / 20 °C 2.1: SnCl4 / CH2Cl2 / -18 °C 3.1: 88 percent / CeCl3*7H2O; NaBH4 / methanol / 0.33 h / 0 °C 4.1: 82 percent / OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 16 h / 20 °C View Scheme

1: SnCl4 / CH2Cl2 / -18 °C 2: 88 percent / CeCl3*7H2O; NaBH4 / methanol / 0.33 h / 0 °C 3: 82 percent / OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 16 h / 20 °C View Scheme

1: 88 percent / CeCl3*7H2O; NaBH4 / methanol / 0.33 h / 0 °C 2: 82 percent / OsO4; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O / 16 h / 20 °C View Scheme

1.1: (Bu3Sn)2O; molecular sieves 3 Angstroem / CHCl3 / 3.5 h / Heating 1.2: 91 percent / Br2 / CHCl3 / 0.05 h / 0 °C 2.1: 43 percent / Et3N / 1 h / 0 °C 3.1: 82 percent / p-TsOH*H2O / 0 - 20 °C View Scheme

1.1: (Bu3Sn)2O; molecular sieves 3 Angstroem / CHCl3 / 3.5 h / Heating 1.2: 91 percent / Br2 / CHCl3 / 0.05 h / 0 °C 2.1: 43 percent / Et3N / 1 h / 0 °C 3.1: 82 percent / p-TsOH*H2O / 0 - 20 °C 4.1: 88 percent / Ac2O; silica gel 60 5.1: 53 percent / H2 / 10percent Pd/C / methanol / 16 h / 20 °C View Scheme