1: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 2: (COCl)2 / dimethylformamide; toluene / 1 h 3: NEt3 / CH2Cl2 4: 100 percent / H2 / Pd/C / ethyl acetate 5: (COCl)2 / toluene; dimethylformamide / 1 h 6: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 7: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 8: NEt3 / CH2Cl2 9: 85 percent / NaN3; 15-crown-6; DMPU View Scheme

1: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 2: (COCl)2 / dimethylformamide; toluene / 1 h 3: NEt3 / CH2Cl2 4: 100 percent / H2 / Pd/C / ethyl acetate 5: (COCl)2 / toluene; dimethylformamide / 1 h 6: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 7: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 8: NEt3 / CH2Cl2 9: 85 percent / NaN3; 15-crown-6; DMPU 10: 59 percent / 2-OH-pyridine; NEt3 11: H2; aq. HCl / Pd/C / methanol View Scheme

1: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 2: (COCl)2 / dimethylformamide; toluene / 1 h 3: NEt3 / CH2Cl2 4: 100 percent / H2 / Pd/C / ethyl acetate 5: (COCl)2 / toluene; dimethylformamide / 1 h 6: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 7: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 8: NEt3 / CH2Cl2 9: 85 percent / NaN3; 15-crown-6; DMPU 10: 59 percent / 2-OH-pyridine; NEt3 View Scheme