Wilkinson's catalyst; hydrogen in toluene T=20°C; P=760.051 Torr; 6 h; Inert atmosphere;

lead(IV) acetate in benzene T=15°C; 72 h; Irradiation;

methanesulfonyl chloride in pyridine 6 h; Heating;

1: 100 percent / tosyl chloride (TsCl) / pyridine / 13 h / Heating; other dehydrating agent 2: 65 percent / H2 / 10percent Pd/C / ethanol / 24 h / 25 °C / 760 Torr 3: 97 percent / CH3SO2Cl / pyridine / 6 h / Heating View Scheme

1: 65 percent / H2 / 10percent Pd/C / ethanol / 24 h / 25 °C / 760 Torr 2: 97 percent / CH3SO2Cl / pyridine / 6 h / Heating View Scheme

1: isopropyl bromide With iodine; magnesium in tetrahydrofuran 0.75 h; Inert atmosphereSonication; 2: LL-Z1271γ in tetrahydrofuran T=0 - 20°C; 3 h; Inert atmosphere; 3: With water; ammonium chloride in tetrahydrofuran T=20°C; 1 h; optical yield given as percent de;

2: TiCl4, Ti(Oi-Pr)4 / CH2Cl2 / 0.17 h / -78 °C 3: 2.) AcOH, piperidine / 2.) PhH, reflux 4: 76 percent / CaCO3 / RhCl3*3H2O / propan-2-ol / 105 °C 5: PhI(OAc)2, I2 / cyclohexane / 50 °C / Irradiation 6: 99 percent / H2 / PtO2 / ethyl acetate / 42 h / 23 °C / 2844.3 Torr 7: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 23 °C 8: diethyl ether / 0 °C 9: 89 percent / PhNMe3Br3 / tetrahydrofuran / 23 °C 10: 90 percent / Li2CO3, LiBr / dimethylformamide / 1 h / 80 - 130 °C 11: DIBAL-H / toluene / -78 - 0 °C 12: tetrapropylammonium perruthenate, NMO, 4 Angstroem mol. sieves / CH2Cl2 / 23 °C 13: 91 percent / LiHMDS, Me3SiCl / tetrahydrofuran / -78 °C 14: 91 percent / Davis oxaziridine / CHCl3 / 0 - 23 °C View Scheme

1: TiCl4, Ti(Oi-Pr)4 / CH2Cl2 / 0.17 h / -78 °C 2: 2.) AcOH, piperidine / 2.) PhH, reflux 3: 76 percent / CaCO3 / RhCl3*3H2O / propan-2-ol / 105 °C 4: PhI(OAc)2, I2 / cyclohexane / 50 °C / Irradiation 5: 99 percent / H2 / PtO2 / ethyl acetate / 42 h / 23 °C / 2844.3 Torr 6: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 23 °C 7: diethyl ether / 0 °C 8: 89 percent / PhNMe3Br3 / tetrahydrofuran / 23 °C 9: 90 percent / Li2CO3, LiBr / dimethylformamide / 1 h / 80 - 130 °C 10: DIBAL-H / toluene / -78 - 0 °C 11: tetrapropylammonium perruthenate, NMO, 4 Angstroem mol. sieves / CH2Cl2 / 23 °C 12: 91 percent / LiHMDS, Me3SiCl / tetrahydrofuran / -78 °C 13: 91 percent / Davis oxaziridine / CHCl3 / 0 - 23 °C View Scheme

2: TiCl4, Ti(Oi-Pr)4 / CH2Cl2 / 0.17 h / -78 °C 3: 2.) AcOH, piperidine / 2.) PhH, reflux 4: 76 percent / CaCO3 / RhCl3*3H2O / propan-2-ol / 105 °C 5: PhI(OAc)2, I2 / cyclohexane / 50 °C / Irradiation 6: 99 percent / H2 / PtO2 / ethyl acetate / 42 h / 23 °C / 2844.3 Torr 7: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 23 °C 8: diethyl ether / 0 °C 9: 89 percent / PhNMe3Br3 / tetrahydrofuran / 23 °C 10: 90 percent / Li2CO3, LiBr / dimethylformamide / 1 h / 80 - 130 °C 11: DIBAL-H / toluene / -78 - 0 °C 12: tetrapropylammonium perruthenate, NMO, 4 Angstroem mol. sieves / CH2Cl2 / 23 °C 13: 91 percent / LiHMDS, Me3SiCl / tetrahydrofuran / -78 °C 14: 91 percent / Davis oxaziridine / CHCl3 / 0 - 23 °C View Scheme

1: PhI(OAc)2, I2 / cyclohexane / 50 °C / Irradiation 2: 99 percent / H2 / PtO2 / ethyl acetate / 42 h / 23 °C / 2844.3 Torr 3: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 23 °C 4: diethyl ether / 0 °C 5: 89 percent / PhNMe3Br3 / tetrahydrofuran / 23 °C 6: 90 percent / Li2CO3, LiBr / dimethylformamide / 1 h / 80 - 130 °C 7: DIBAL-H / toluene / -78 - 0 °C 8: tetrapropylammonium perruthenate, NMO, 4 Angstroem mol. sieves / CH2Cl2 / 23 °C 9: 91 percent / LiHMDS, Me3SiCl / tetrahydrofuran / -78 °C 10: 91 percent / Davis oxaziridine / CHCl3 / 0 - 23 °C View Scheme