Pd(sparteine)Cl2; 6-methoxy-2-naphthol sodium salt; oxygen; (-)-sparteine in chloroform T=35°C; 48 h; Molecular sieve; optical yield given as percent ee;

sodium hydrogencarbonate in water; benzene

1: 61 percent / H2 / Pd/C / ethyl acetate / 4 h 2: 0.12 HCl / Heating View Scheme

hydrogenchloride in isopropyl alcohol T=60°C; 3 h; Title compound not separated from byproducts.;

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

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

1.1: 100 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 2.1: 84 percent / (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -35 °C 3.1: 90 percent / 4-(dimethylamino)pyridine / acetonitrile / 5 h 4.1: 85 percent / IBr / toluene; CH2Cl2 / 1 h / -85 °C 5.1: 96 percent / K2CO3; methanol / 2 h / 20 °C 6.1: 92 percent / PPh3; DEAD / tetrahydrofuran / 2 h / 20 °C 7.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C 8.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 9.1: CuI / diethyl ether / 0.25 h / -30 °C 9.2: 92 percent / diethyl ether / 0.5 h / -40 °C 10.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 11.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 12.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 13.1: tetrahydrofuran / 0 - 20 °C 14.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 15.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 16.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 17.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme

1.1: 90 percent / 4-(dimethylamino)pyridine / acetonitrile / 5 h 2.1: 85 percent / IBr / toluene; CH2Cl2 / 1 h / -85 °C 3.1: 96 percent / K2CO3; methanol / 2 h / 20 °C 4.1: 92 percent / PPh3; DEAD / tetrahydrofuran / 2 h / 20 °C 5.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C 6.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 7.1: CuI / diethyl ether / 0.25 h / -30 °C 7.2: 92 percent / diethyl ether / 0.5 h / -40 °C 8.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 9.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 10.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 11.1: tetrahydrofuran / 0 - 20 °C 12.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 13.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 14.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 15.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme

1.1: 92 percent / PPh3; DEAD / tetrahydrofuran / 2 h / 20 °C 2.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C 3.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 4.1: CuI / diethyl ether / 0.25 h / -30 °C 4.2: 92 percent / diethyl ether / 0.5 h / -40 °C 5.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 6.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 7.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 8.1: tetrahydrofuran / 0 - 20 °C 9.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 10.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 11.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 12.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme

1.1: 96 percent / K2CO3; methanol / 2 h / 20 °C 2.1: 92 percent / PPh3; DEAD / tetrahydrofuran / 2 h / 20 °C 3.1: 77 percent / K2CO3; methanol / H2O / 2 h / 20 °C 4.1: 96 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 3 h / 20 °C 5.1: CuI / diethyl ether / 0.25 h / -30 °C 5.2: 92 percent / diethyl ether / 0.5 h / -40 °C 6.1: 97 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 7.1: 88 percent / dimethylformamide; H2O / 20 h / 50 °C 8.1: 95 percent / triethylamine / CH2Cl2 / 6 h / 20 °C 9.1: tetrahydrofuran / 0 - 20 °C 10.1: 1.83 g / NaOH; H2O2 / H2O; ethanol; tetrahydrofuran / 1 h / 20 °C 11.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 0.25 h / 20 °C 12.1: 82 percent / tetrahydrofuran / 13 h / 65 °C 13.1: HCl / propan-2-ol / 3 h / 60 °C View Scheme