1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 80 percent / TsOH*H2O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h 3: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 100 percent / KOH / methanol / 3 h / Ambient temperature 8: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h View Scheme

1: 97 percent / H2 / RuBr2<(R)-binap> / ethanol / 145 h / 20 °C / 76000.1 Torr 2: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 3: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr View Scheme

1.1: TiCl4 / CH2Cl2 / 0.5 h 1.2: 75 percent / BH3-pyridine complex / tetrahydrofuran / 1 h / -78 °C 2.1: 95 percent / LiOH / tetrahydrofuran; H2O / 24 h View Scheme

1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 80 percent / TsOH*H2O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h 3: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 100 percent / KOH / methanol / 3 h / Ambient temperature 8: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 9: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature View Scheme

1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 80 percent / TsOH*H2O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h 3: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 100 percent / KOH / methanol / 3 h / Ambient temperature 8: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 9: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 10: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 11: H2 / 10percent Pd/C / ethanol / 16 h 12: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: 97 percent / H2 / RuBr2<(R)-binap> / ethanol / 145 h / 20 °C / 76000.1 Torr 2: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 3: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr 4: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 5: 4N HCl / dioxane / 0.5 h / Ambient temperature 6: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 7: 4N HCl / dioxane / 0.5 h / Ambient temperature 8: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 80 percent / TsOH*H2O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h 3: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 100 percent / KOH / methanol / 3 h / Ambient temperature 8: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h 9: 86 percent / trifluoroacetic acid / 1 h / Ambient temperature 10: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature View Scheme

hydrogen; (S)-BinapRuBr2 in ethanol T=18 - 21°C; P=76000.1 Torr; 145 h; threo/erythro ratio 9/91, ee = 99percent; Yields of byproduct given;

hydrogen; [(R)-BINAP]RuBr2 in ethanol T=20°C; P=76000.1 Torr; 145 h;

1.1: TiCl4 / CH2Cl2 / 0.5 h 1.2: 75 percent / BH3-pyridine complex / tetrahydrofuran / 1 h / -78 °C 2.1: 95 percent / LiOH / tetrahydrofuran; H2O / 24 h 3.1: HCOOH / 6 h / 20 °C View Scheme