1: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 2: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr View Scheme

sodium hydroxide in tetrahydrofuran 2 h;

1: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 2: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr 3: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 4: 4N HCl / dioxane / 0.5 h / Ambient temperature 5: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 6: 4N HCl / dioxane / 0.5 h / Ambient temperature 7: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C 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;

hydrogen; [(R)-BINAP]RuBr2 in ethanol T=18 - 21°C; P=76000.1 Torr; ee = 97percent; Yields of byproduct given;

hydrogen; triethylamine; palladium on activated charcoal T=25°C; 24 h;

1: 1.) CDI 2: NaBH4 / ethanol / -78 °C View Scheme

1: 35 percent / Et3N, LiClO4 / CH2Cl2 / 4 h / -78 °C 2: 81 percent / H2, Et3N / Pd/C / ethyl acetate / 15 h / 760 Torr View Scheme

1: ethyl acetate With lithium diisopropyl amide in tetrahydrofuran; hexane; ethylbenzene T=-78°C; 2: [(1S)-1-formyl-2-phenylethyl]-carbamic acid 1,1-dimethylethyl ester in tetrahydrofuran; hexane; ethylbenzene T=-78 - 0°C;