1: KHSO4 2: 1) O2, 2) H2 / 2) Raney-Ni / 1) 50 deg C, toluene, 2) 100 deg C, 16 MPa View Scheme

tris(triphenylphosphine)ruthenium(II) chloride; ethylene,methyl acetate; carbon monoxide

triethylamine; palladium on activated charcoal in toluene T=200°C; 12 h;

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C 2: bis(1,1-diphenylphosphino)methane; tetracarbonylbis(μ-chloro)dirhodium(I) / ethylene glycol dimethyl ether / 20 h / 65 °C / |Inert atmosphere View Scheme

cerium(III) chloride; lithium hydride in tetrahydrofuran T=-78°C; 72 h;

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

(1R,2R)-(+)-1,2-diphenylethylenediamine; potassium tert-butylate; cyclohexanone; [Ru(II)(η6-benzene)(μ-Cl)Cl]2; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl in tetrahydrofuran T=60°C; 20 h;

triethylamine; palladium on activated charcoal in toluene T=200°C; 12 h;

[RhCl(η2:η2-cycloocta-1,5-diene)]2; potassium tert-butylate; triphenylphosphine in tetrahydrofuran T=60°C; 15 h; Molecular sieve; optical yield given as percent de;

[RhCl(η2:η2-cycloocta-1,5-diene)]2; potassium tert-butylate; triphenylphosphine in tetrahydrofuran T=40°C; 18 h; optical yield given as percent de;