tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C;

anthracene; triethylamine in toluene T=20°C; 1 h; Irradiation;

1: C35H60O2Si2 With bis(cyclohexanyl)borane; diethylzinc; (+)-DAIB in hexane T=-20 - 0°C; 2: formyl cyclopropane in hexane T=0°C;

1-(9-anthryl)ethanone in tert-butyl methyl ether 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 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 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 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 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 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 View Scheme