sodium hydroxide in dichloromethane; water Product distribution / selectivity;

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 1.2: 0 - 20 °C 2.1: sodium tetrahydroborate / methanol / 20 °C 3.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 7.1: dichloromethane / 1 h / 20 °C 8.1: triethylamine / dichloromethane 9.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere 2.2: -15 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 3.2: 0 - 20 °C 4.1: sodium tetrahydroborate / methanol / 20 °C 5.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C 6.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 7.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C 8.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 9.1: dichloromethane / 1 h / 20 °C 10.1: triethylamine / dichloromethane 11.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: dichloromethane / 1 h / 20 °C 2: triethylamine / dichloromethane 3: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 12 h / -78 - 0 °C 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr 3.1: triethylamine / dichloromethane / 0.08 h / 20 °C 4.1: triethylamine / dichloromethane 5.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr 2: triethylamine / dichloromethane / 0.08 h / 20 °C 3: triethylamine / dichloromethane 4: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: triethylamine / dichloromethane / 0.08 h / 20 °C 2: triethylamine / dichloromethane 3: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 2 h / -78 °C 2.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 3.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 5.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 5.2: 16 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 8.1: water; acetic acid / 1.5 h / Heating 9.1: pyridine / dichloromethane / 16 h / 20 °C 10.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere 11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 11.2: 12 h / -78 - 0 °C 12.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr 13.1: triethylamine / dichloromethane / 0.08 h / 20 °C 14.1: triethylamine / dichloromethane 15.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 2.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 4.2: 16 h / 20 °C 5.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 6.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 7.1: water; acetic acid / 1.5 h / Heating 8.1: pyridine / dichloromethane / 16 h / 20 °C 9.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere 10.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 10.2: 12 h / -78 - 0 °C 11.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr 12.1: triethylamine / dichloromethane / 0.08 h / 20 °C 13.1: triethylamine / dichloromethane 14.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Cooling with ice 1.2: 20 °C / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere 3.2: -15 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 4.2: 0 - 20 °C 5.1: sodium tetrahydroborate / methanol / 20 °C 6.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C 7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 8.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C 9.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 5 °C 10.1: dichloromethane / 1 h / 20 °C 11.1: triethylamine / dichloromethane 12.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme