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 5.1: DHP / |Acidic conditions 6.1: base 7.1: water / |Acidic conditions 8.1: benzenesulfonyl chloride; pyridine 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 5.1: DHP / |Acidic conditions 6.1: base 7.1: water / |Acidic conditions 8.1: benzenesulfonyl chloride; pyridine 9.1: diethylazodicarboxylate; triphenylphosphine View Scheme

1,4-dioxane; methanol; nickel T=100°C; P=73550.8 Torr; Hydrogenation.und Erwaermen des Reaktionsprodukts mit aethanol.Kalilauge;

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 5.1: DHP / |Acidic conditions 6.1: base 7.1: water / |Acidic conditions 8.1: benzenesulfonyl chloride; pyridine View Scheme

1: With hydrogen; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl; ruthenium trichloride in methanol T=40 - 50°C; P=3361.46 Torr; 20 h; 2: With lithium hydroxide in tetrahydrofuran; water

sodium tetrahydroborate in methanol T=0°C;

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

1: p-toluenesulfonic acid / benzene / 24 h / Heating 2: aq. NaOH / methanol / 6 h View Scheme

potassium carbonate; pentan-2-one Erwaermen des Reaktionsprodukts mit wss.-methanol. Kalilauge;

1: With hydrogen; (S)-RuBINAP in hydrogenchloride; methanol P=1034.3 Torr; 2: P=2585.74 Torr; 15 h; Heating; Title compound not separated from byproducts;