1: With 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile P=760.051 Torr; 0.75 h; 2: With tributylphosphine; di-tert-butylazodicarboxylate in acetonitrile Mitsunobu reaction; P=760.051 Torr; Inert atmosphere;

triethylamine in dichloromethane T=20°C; 17 h;

sodium tetrahydroborate; nickel dichloride in tetrahydrofuran; methanol 0.5 h; Ambient temperature;

1: NaBH4 / methanol / 1 h / Ambient temperature 2: 85 percent / Et3N / benzene / 2 h / Ambient temperature 3: 94 percent / aq. NaIO4 / methanol / 20 h / Ambient temperature 4: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 5: 57 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 85 percent / Et3N / benzene / 2 h / Ambient temperature 2: 94 percent / aq. NaIO4 / methanol / 20 h / Ambient temperature 3: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 4: 57 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: AcOH / ethanol / 20 h / Heating 2: NaBH4 / methanol / 1 h / Ambient temperature 3: 85 percent / Et3N / benzene / 2 h / Ambient temperature 4: 94 percent / aq. NaIO4 / methanol / 20 h / Ambient temperature 5: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 6: 57 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 94 percent / aq. NaIO4 / methanol / 20 h / Ambient temperature 2: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 3: 57 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 2: 57 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

L-Selectridereg; in tetrahydrofuran T=20°C; 72 h;

sodium iodide in acetonitrile T=60°C; 7 h;