tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C;

1-(9-anthryl)ethanone in acetone T=10°C; UV-irradiation; Product distribution / selectivity;

1-(9-anthryl)ethanone in acetone T=10°C; UV-irradiation; Product distribution / selectivity;

1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature 2: 84 percent 3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 5: N-methylmorpholine N-oxide, selenium dioxide 6: imidazole / dimethylformamide 7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme

1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C 2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 3: NaHCO3 / aq. ethanol / Heating 5: N-methylmorpholine N-oxide, selenium dioxide 6: imidazole / dimethylformamide 7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme

1: liq. SO2 / 0.5 h / Heating 2: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C 3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 4: NaHCO3 / aq. ethanol / Heating 6: N-methylmorpholine N-oxide, selenium dioxide 7: imidazole / dimethylformamide 8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme

1.1: bis(cyclohexanyl)borane; diethylzinc; (+)-DAIB / hexane / -20 - 0 °C 1.2: 0 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1.1: n-hexyl lithium / -78 °C 2.1: bis(cyclohexanyl)borane; diethylzinc; (+)-DAIB / hexane / -20 - 0 °C 2.2: 0 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C View Scheme

2: N-methylmorpholine N-oxide, selenium dioxide 3: imidazole / dimethylformamide 4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme

1: N-methylmorpholine N-oxide, selenium dioxide 2: imidazole / dimethylformamide 3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme