3,6-bis(triphenylphosphonium)cyclohexene peroxodisulfate in water; acetonitrile 0.5 h; Heating;

Reaktion ueber mehrere Stufen;

5 Pd(II)/C(eggshell); hydrogen in ethyl acetate T=20°C;

1: DIBAL 2: periodic acid; RuCl3 3: NaN3 / Cu(NO3)2 / H2O / 1.5 h / 65 °C 4: NaBH4 / Cu(NO3)2 / H2O / 0.5 h / 0 °C View Scheme

1: 5 Pd(II)/C(eggshell); hydrogen / ethyl acetate / 20 °C 2: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Inert atmosphere View Scheme

1.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / diethyl ether / 1 h / 0 °C / Inert atmosphere 1.2: Cooling with ice 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 0 °C 3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 0.25 h / 70 °C / Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; di(n-butyl)tin oxide; triethylamine / dichloromethane / 3 h / 0 - 20 °C 5.1: potassium carbonate / methanol / 1 h / 0 - 25 °C 6.1: (S,S)-(salen)Co(OAc) complex; water / tetrahydrofuran / 14 h / 0 - 25 °C 7.1: isopropyl alcohol / 5 h / 50 °C 8.1: triethylamine / dichloromethane / 12.5 h / 0 - 20 °C 9.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 25 °C 9.2: 29 h 10.1: triethylamine / dichloromethane / 2 h / 25 °C View Scheme

1: (DHQ)2PHAL; K2[OsO2(OH)2]; LiOH / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 2: 87 percent / HCl / methanol / Heating 3: Et3N / CH2Cl2 / 0 - 20 °C 4: 89 percent / p-toluenesulfonic acid / CH2Cl2 / 20 °C 5: 76 percent / DIBAL-H / CH2Cl2 / -78 - 20 °C 6: 60 percent / tetrahydrofuran / 0 - 20 °C 7: 90 percent / H2 / Pd/C / ethyl acetate; methanol 8: 67 percent / AcOH / toluene / Heating 9: 73 percent / cc. HCl / 80 °C View Scheme

1.1: 94 percent / DIBAL-H / toluene; tetrahydrofuran / 2 h / -78 - -10 °C 2.1: 81 percent / PCC / CH2Cl2 / 2.5 h / 20 °C 3.1: PPh3 / CH2Cl2 / 0.05 h / 0 °C 3.2: 84 percent / CH2Cl2 / 3 h / 0 °C View Scheme