4-(N,N-dimethlyamino)pyridine; potassium carbonate in dichloromethane T=40°C; 0.5 h; Microwave irradiation; optical yield given as percent ee;

nonafluoro-n-butanesulfonyl fluoride; triethylamine in dichloromethane T=20°C; 1 h;

1: lithium aluminium tetrahydride / tetrahydrofuran 2: 4-(N,N-dimethlyamino)pyridine; potassium carbonate / dichloromethane / 0.5 h / 40 °C / Microwave irradiation View Scheme

1: lithium borohydride / tetrahydrofuran / 0 - 20 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere View Scheme

1: triethylamine / dichloromethane / 0 - 25 °C 2: lithium borohydride / tetrahydrofuran / 0 - 20 °C 3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere View Scheme

1: 92 percent / Et3N / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 4 h 2: 1) TsCl, Et3N, DMAP, 2) NaH / 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h View Scheme

1: LiAlH4 2: TsCl; Et3N; 4-dimethylaminopyridine View Scheme

1: diisopropylethylamine 2: LiAlH4 3: TsCl; Et3N; 4-dimethylaminopyridine View Scheme

4-(N,N-dimethlyamino)pyridine; sodium hydride; triethylamine; p-toluenesulfonyl chloride 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 75 percent / potassium t-butoxide 2: 90 percent / HBr / H2O / 16 h / Heating 3: 67 percent / dioxane / 16 h / Heating 4: 57 percent / NaH / tetrahydrofuran / 1.08 h 5: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 6: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 7: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 8: toluene / 5 h / 90 °C 9: NaOH / methanol / 2 h / Ambient temperature 10: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 11: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 12: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme