sodium tetrahydroborate; cerium(III) chloride in water; isopropyl alcohol T=0°C;

1: 8N Jones reagent / 0 °C 2: oxalylchloride/DMF, 1drop / benzene / 1 h 3: 16 h / 0 °C 4: <Rh(OAc)2>2 / 2 h / Ambient temperature 5: 60 percent / NaBH4/CeCl3 / propan-2-ol; H2O / 0 °C View Scheme

1: 16 h / 0 °C 2: <Rh(OAc)2>2 / 2 h / Ambient temperature 3: 60 percent / NaBH4/CeCl3 / propan-2-ol; H2O / 0 °C View Scheme

1: oxalylchloride/DMF, 1drop / benzene / 1 h 2: 16 h / 0 °C 3: <Rh(OAc)2>2 / 2 h / Ambient temperature 4: 60 percent / NaBH4/CeCl3 / propan-2-ol; H2O / 0 °C View Scheme

1: <Rh(OAc)2>2 / 2 h / Ambient temperature 2: 60 percent / NaBH4/CeCl3 / propan-2-ol; H2O / 0 °C View Scheme

1: 1.) LiNH2/NH3, 2.) 1N HCl / -33 deg C 2: 8N Jones reagent / 0 °C 3: oxalylchloride/DMF, 1drop / benzene / 1 h 4: 16 h / 0 °C 5: <Rh(OAc)2>2 / 2 h / Ambient temperature 6: 60 percent / NaBH4/CeCl3 / propan-2-ol; H2O / 0 °C View Scheme