1: 1,1-dimethylethylmagnesium chloride / tetrahydrofuran / 22.5 h / 60 °C 2: hydrogen View Scheme

1.1: Ru(OAc)2((R)-MeOBIPHEP); hydrogenchloride / water; methanol / 0.5 h / 20 °C / |Autoclave; |Sealed tube; |Inert atmosphere 1.2: 4.42 h / 80 °C / 22502.3 - 30003 Torr / |Autoclave; |Sealed tube; |Inert atmosphere 2.1: potassium hydrogencarbonate; 4-(N,N-dimethlyamino)pyridine / water; methanol; toluene / 3.5 h / 11 °C 3.1: 1,1-dimethylethylmagnesium chloride / tetrahydrofuran / 22.5 h / 60 °C 4.1: hydrogen View Scheme

potassium hydroxide; toluene-4-sulfonic acid 1.) dioxane, water, RT, overnight, 2.) chloroform, RT, 2 h; Yield given. Multistep reaction;

1: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 2: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 3: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 4: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 5: benzenesulfonylchloride, pyridine / 0 °C 6: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme

1: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 2: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 3: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 4: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 5: benzenesulfonylchloride, pyridine / 0 °C 6: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C 7: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 2: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 3: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 4: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 5: benzenesulfonylchloride, pyridine / 0 °C 6: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme