TiCl2(OPri)2 in dichloromethane T=-78 - 25°C; 20 h;

titanium tetrachloride

1: 91 percent / Mg / diethyl ether 2: 85 percent / H2CrO4 / H2O; diethyl ether 3: 79 percent / p-TsOH*H2O / benzene / 48 h / Heating 4: 4.28 g / BH3-Me2S / tetrahydrofuran 5: pyridine 6: 85 percent / Li2CuCl4 / tetrahydrofuran 8: 97 percent / p-TsOH*H2O / benzene 9: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 10: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

1: 85 percent / H2CrO4 / H2O; diethyl ether 2: 79 percent / p-TsOH*H2O / benzene / 48 h / Heating 3: 4.28 g / BH3-Me2S / tetrahydrofuran 4: pyridine 5: 85 percent / Li2CuCl4 / tetrahydrofuran 7: 97 percent / p-TsOH*H2O / benzene 8: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 9: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

1: pyridine 2: 85 percent / Li2CuCl4 / tetrahydrofuran 4: 97 percent / p-TsOH*H2O / benzene 5: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 6: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

1: 97 percent / p-TsOH*H2O / benzene 2: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 3: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

1: 4.28 g / BH3-Me2S / tetrahydrofuran 2: pyridine 3: 85 percent / Li2CuCl4 / tetrahydrofuran 5: 97 percent / p-TsOH*H2O / benzene 6: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 7: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

2: 97 percent / p-TsOH*H2O / benzene 3: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 4: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

1: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 2: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme

1: 85 percent / Li2CuCl4 / tetrahydrofuran 3: 97 percent / p-TsOH*H2O / benzene 4: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF 5: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C View Scheme