1: 17.1 g / LiAlH4 / diethyl ether / 0.25 h / -78 °C 2: 95 percent / 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide, tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 3: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 4: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 5: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 6: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C 7: 62 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

lithium aluminium tetrahydride in diethyl ether T=-78°C; 0.25 h;

1: 17.1 g / LiAlH4 / diethyl ether / 0.25 h / -78 °C 2: 95 percent / 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide, tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 3: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 4: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 5: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 6: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C View Scheme