1: chiral binaphthyl-based ammonium salt; potassium hydroxide / toluene; H2O / 2 h / 0 °C 2: HCl / tetrahydrofuran / 0 °C View Scheme

1: chiral binaphthyl-based ammonium salt; potassium hydroxide / toluene; H2O / 2 h / 0 °C 2: HCl / tetrahydrofuran / 0 °C View Scheme

1: 60 percent / 3-chloroperbenzoic acid / CH2Cl2 / 0 °C 2: 3-chloroperbenzoic acid 3: 56 percent / NaBH4 / propan-2-ol; H2O / 4 h / Ambient temperature View Scheme

1: 3-chloroperbenzoic acid 2: 56 percent / NaBH4 / propan-2-ol; H2O / 4 h / Ambient temperature View Scheme

sodium hydroxide; sodium nitrate in methanol T=20°C; Rate constant;

sodium hydroxide; sodium nitrate in methanol T=20°C; Rate constant;

1: 69 percent / Et3N, 1-hydroxybenzotriazole hydrate (HOBt), 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC) / dimethylformamide / 12 h / 23 °C 2: 51 percent / TFA / CH2Cl2 / 2.5 h / 23 °C View Scheme

1: 70 percent / benzene / 0.5 h / Ambient temperature 2: 91 percent / TFA / CH2Cl2 / 2 h / Ambient temperature 3: 82 percent / SOCl2 / CH2Cl2 / 2 h / Heating 4: NaHCO3 / CH2Cl2 / 0.25 h 5: 4-(aminomethyl)piperidine silica reagent / CH2Cl2 / 0.25 h 6: NaHCO3 / CH2Cl2 / 0.25 h 7: 4-(aminomethyl)piperidine silica reagent / CH2Cl2 / 0.25 h 8: NaHCO3 / CH2Cl2 / 0.25 h 9: 4-(aminomethyl)piperidine silica reagent / CH2Cl2 / 0.25 h 10: NaHCO3 / CH2Cl2 / 0.33 h 11: 58 percent / H2 / Pd/C / ethanol; ethyl acetate / 24 h / 2327.17 Torr / Ambient temperature View Scheme

1: triphenylphosphine, ethylazodicarboxylate / tetrahydrofuran / 1 h 2: 33percent HBr/AcOH View Scheme

1: 97 percent / triethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / CHCl3; tetrahydrofuran / Ambient temperature 2: 80 percent / 1N aq. NaOH / ethanol / 2 h / Ambient temperature 3: 82 percent / N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide, NH3 / tetrahydrofuran / Ambient temperature 4: TFA / CH2Cl2 / 3 h / 0 - 20 °C 5: <bis(trifluoroacetoxy)iodo>benzene / acetonitrile; H2O / 3 h View Scheme