triethylamine in water; N,N-dimethyl-formamide 1 h;

1: 90 percent / diisobutyl aluminum hydride / diethyl ether; hexane / 1 h / 0 °C 2: 1.) diisopropyl D-(-)-tartrate, titanium tetraisopropoxide, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -22 deg C, 1 h, 2.) CH2Cl2, isooctane, -20 deg C, 20 h 3: 68 percent / titanium tetraisopropoxide / CH2Cl2 / 24 h / Heating 4: 1.) NaIO4, RuCl3, 2.) NaHCO3 / 1.) CH3CN, CCl4, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h View Scheme

1: 1.) diisopropyl D-(-)-tartrate, titanium tetraisopropoxide, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -22 deg C, 1 h, 2.) CH2Cl2, isooctane, -20 deg C, 20 h 2: 68 percent / titanium tetraisopropoxide / CH2Cl2 / 24 h / Heating 3: 1.) NaIO4, RuCl3, 2.) NaHCO3 / 1.) CH3CN, CCl4, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h View Scheme

1: 68 percent / titanium tetraisopropoxide / CH2Cl2 / 24 h / Heating 2: 1.) NaIO4, RuCl3, 2.) NaHCO3 / 1.) CH3CN, CCl4, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h View Scheme

ruthenium trichloride; sodium periodate; sodium hydrogencarbonate 1.) CH3CN, CCl4, water, room temp., 17 h, 2.) methanol, ultrasonic irrad., room temp., 15 h; Yield given. Multistep reaction;