ethanol

1.1: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / CH2Cl2 1.2: trimethylphosphite; 4-dimethylaminopyridine; triethylamine / CH2Cl2 2.1: 45 percent / CuI / diethyl ether / 1.17 h / -30 °C 3.1: 2,4,6-collidine hydrochloride; manganese; 1,4-cyclohexadiene / ((1S,2R,5S)-2-i-Pr-5-Me-cyclohex-1-yl)Cp)2TiCl2 / tetrahydrofuran / 20 °C View Scheme

1: 90 percent / PBr3,Py / diethyl ether / a.) standing overnight b.) 2h reflux 2: 70 percent / benzene / 16 h / Heating 3: 78 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 140 - 145 °C 4: 90 percent / LiAlH4 / diethyl ether / a.) reflux while adding reagent b.) room temperature overnight c.) 30 min reflux View Scheme

1: 90 percent / PBr3,Py / diethyl ether / a.) standing overnight b.) 2h reflux 2: 70 percent / benzene / 16 h / Heating 3: 78 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 140 - 145 °C 4: 90 percent / LiAlH4 / diethyl ether / a.) reflux while adding reagent b.) room temperature overnight c.) 30 min reflux 5: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h View Scheme

pyridine; phosphorus tribromide in diethyl ether a.) standing overnight b.) 2h reflux;

1: P(OPh)3 / [Ir(COD)Cl]2 / 4 h / 50 °C View Scheme

pyridine in benzene Ambient temperature;