n-butyllithium 1.) THF, hexane, -30 deg C, 45 min, 2.) THF, -30 to -10 deg C, 90 min; Yield given. Multistep reaction;

1.1: toluene / 8 h / 60 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: Pd(1,3-bis(diphenylphosphino)-propane)Cl2; lithium triethylborohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere View Scheme

diisobutylaluminium hydride in diethyl ether; dichloromethane T=-70°C; 0.75 h;

chiral binaphthalenedioxaphoshepin derivative; hydrogen; [rhodium(I)(carbonyl)2(acetylacetonate)] in benzene T=60°C; 6 h;

1: 60 percent / LAH / tetrahydrofuran / 20 °C 2: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme

dimethyl sulfoxide; triethylamine in dichloromethane; water

1: 93 percent / CH2Cl2 / Heating 2: 79 percent / H2 / Pd/CaCO3 / methanol / 1.5 h 3: 68 percent / diisobutylaluminium hydride / CH2Cl2; diethyl ether / 0.75 h / -70 °C View Scheme

1: 79 percent / H2 / Pd/CaCO3 / methanol / 1.5 h 2: 68 percent / diisobutylaluminium hydride / CH2Cl2; diethyl ether / 0.75 h / -70 °C View Scheme

1: H2 / Pd/C / methanol 2: (COCl)2; Et3N / dimethylsulfoxide / -78 °C View Scheme