hydrogen; platinum in ethyl acetate T=20°C; P=34202.3 Torr; 48 h;

hydrogen; lt;(S)-BINAPgt;chloro(p-cymene)ruthenium chloride in methanol T=60°C; P=76005.1 Torr; 18 h;

1.1: NaH; BuLi / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / Heating 2.1: copper(II) diacetate / aq. methanol 2.2: NaH; KI; Bu4NBr / tetrahydrofuran / Heating 3.1: H2 / (R)-[BINAP-Ru(II)Cl-p-cymene](1+)*Cl(1-) / methanol / 18 h / 60 °C / 76005.1 Torr View Scheme

1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h 2: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature 3: p-TsOH, / CHCl3 / Ambient temperature 4: Jones' reagent / acetone / 1 h / 10 °C 5: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature View Scheme

1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h 2: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature 3: p-TsOH, / CHCl3 / Ambient temperature 4: Jones' reagent / acetone / 1 h / 10 °C 5: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature View Scheme

1: p-TsOH, / CHCl3 / Ambient temperature 2: Jones' reagent / acetone / 1 h / 10 °C 3: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature View Scheme

1: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 2: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 3: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 4: benzenesulfonylchloride, pyridine / 0 °C 5: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C 6: 1.) 1 N KOH, 2.) p-TsOH / 1.) dioxane, water, RT, overnight, 2.) chloroform, RT, 2 h View Scheme

1: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature 2: p-TsOH, / CHCl3 / Ambient temperature 3: Jones' reagent / acetone / 1 h / 10 °C 4: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature View Scheme

1: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 2: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 3: benzenesulfonylchloride, pyridine / 0 °C 4: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C 5: 1.) 1 N KOH, 2.) p-TsOH / 1.) dioxane, water, RT, overnight, 2.) chloroform, RT, 2 h View Scheme

1: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 2: benzenesulfonylchloride, pyridine / 0 °C 3: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C 4: 1.) 1 N KOH, 2.) p-TsOH / 1.) dioxane, water, RT, overnight, 2.) chloroform, RT, 2 h View Scheme