titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate in dichloromethane; 1,2-dichloro-ethane T=-30°C; 96 h;

diethyl (2R,3R)-tartrate Sharpless epoxidation; Yield given;

1: H2 / Lindlar catalyst / benzene / Ambient temperature 2: 74 percent / (D)-(-)-DIPT, Ti(OiPr)4, TBHP, 4A MS / CH2Cl2 / 64 h / -30 °C View Scheme

1: 1.) KOH / 1.) water, 2,5 h, r.t.; 2.) DMF, 5 h, r.t. 2: 58 percent / NEt3, dimethylaminopyridine / CH2Cl2 / 1 h / Ambient temperature 3: 91 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C 4: 95 percent / Ti(OiPr)4, diethyl-(-)-D-tartrate, 4.1 N t-butylhydroperoxide / CH2Cl2; 1,2-dichloro-ethane / 96 h / -30 °C View Scheme

1: 58 percent / NEt3, dimethylaminopyridine / CH2Cl2 / 1 h / Ambient temperature 2: 91 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C 3: 95 percent / Ti(OiPr)4, diethyl-(-)-D-tartrate, 4.1 N t-butylhydroperoxide / CH2Cl2; 1,2-dichloro-ethane / 96 h / -30 °C View Scheme

1: 58 percent / NEt3, dimethylaminopyridine / CH2Cl2 / 1 h / Ambient temperature 2: 91 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C 3: 95 percent / Ti(OiPr)4, diethyl-(-)-D-tartrate, 4.1 N t-butylhydroperoxide / CH2Cl2; 1,2-dichloro-ethane / 96 h / -30 °C View Scheme

1: 91 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C 2: 95 percent / Ti(OiPr)4, diethyl-(-)-D-tartrate, 4.1 N t-butylhydroperoxide / CH2Cl2; 1,2-dichloro-ethane / 96 h / -30 °C View Scheme