1,4-diaza-bicyclo[2.2.2]octane in isopropyl alcohol T=20°C; 1 h;

aluminum oxide in diethyl ether 2 h;

1.1: 84 percent / (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -35 °C 2.1: 90 percent / 4-(dimethylamino)pyridine / acetonitrile / 5 h 3.1: 85 percent / IBr / toluene; CH2Cl2 / 1 h / -85 °C 4.1: 96 percent / K2CO3; methanol / 2 h / 20 °C 5.1: 92 percent / PPh3; DEAD / tetrahydrofuran / 2 h / 20 °C 6.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C 7.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 8.1: CuI / diethyl ether / 0.25 h / -30 °C 8.2: 92 percent / diethyl ether / 0.5 h / -40 °C 9.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 10.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 11.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 12.1: tetrahydrofuran / 0 - 20 °C 13.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 14.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 15.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 16.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme

hydrogen; platinum in acetic acid

1: With Zhan 1b catalyst in dichloromethane T=55°C; Olefin cross-metathesis; 96 h; Inert atmosphere; 2: With ammonium acetate; acetic acid in ethanol T=55°C; 24 h;

1: Zhan 1b catalyst / dichloromethane / 48 h / Inert atmosphere; Reflux 2: ammonium acetate; acetic acid / ethanol / 24 h / 55 °C View Scheme

1,4-diaza-bicyclo[2.2.2]octane in isopropyl alcohol T=20°C; 1 h;

aluminum oxide in diethyl ether 2 h;

lithium aluminium tetrahydride; Darvon's alcohol; silver(l) oxide 1) Et2O, 0 deg C to room temp.; 2) reflux, 24 h. Investigation of the enantiomeric excess; Product distribution;

boron trifluoride diethyl etherate T=20°C; 3 h;