trifluoroacetic acid in dichloromethane T=20°C; 5 h; Inert atmosphere;

1: Corey-AD-ligand-α non MeI salt; methanesulfonamide; K3[Fe(CN)6] / K2OsO4*2H2O; K2CO3 / 2-methyl-propan-2-ol; H2O / 18.5 h / 0 °C 2: 78 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 12.25 h / 0 - 20 °C 3: triphenylphosphine; diethyl azodicarboxylate / benzene / 4.25 h / 20 °C 4: 697 mg / NH4OH / methanol; H2O / 1.5 h / 20 °C 5: 87 percent / N-ethyldiisopropylamine / CH2Cl2 / 66 h / 20 °C 6: 100 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C 7: 92 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 18.5 h / 20 °C 8: 83 percent / CF3CO2H / tetrahydrofuran; H2O / 22 h / 20 °C 9: 96 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 14 h / 20 °C 10: 19 percent / CH3CO2H / propan-2-ol; H2O 11: triethylamine / toluene / 1 h / 20 °C 12: triethylamine; 4-(dimethylamino)pyridine / toluene / 3.5 h / 80 °C 13: 90 percent / trifluoroacetic acid / CH2Cl2 / 7.5 h / 20 °C View Scheme

1: 87 percent / N-ethyldiisopropylamine / CH2Cl2 / 66 h / 20 °C 2: 100 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C 3: 92 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 18.5 h / 20 °C 4: 83 percent / CF3CO2H / tetrahydrofuran; H2O / 22 h / 20 °C 5: 96 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 14 h / 20 °C 6: 19 percent / CH3CO2H / propan-2-ol; H2O 7: triethylamine / toluene / 1 h / 20 °C 8: triethylamine; 4-(dimethylamino)pyridine / toluene / 3.5 h / 80 °C 9: 90 percent / trifluoroacetic acid / CH2Cl2 / 7.5 h / 20 °C View Scheme

1: triphenylphosphine; diethyl azodicarboxylate / benzene / 4.25 h / 20 °C 2: 697 mg / NH4OH / methanol; H2O / 1.5 h / 20 °C 3: 87 percent / N-ethyldiisopropylamine / CH2Cl2 / 66 h / 20 °C 4: 100 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C 5: 92 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 18.5 h / 20 °C 6: 83 percent / CF3CO2H / tetrahydrofuran; H2O / 22 h / 20 °C 7: 96 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 14 h / 20 °C 8: 19 percent / CH3CO2H / propan-2-ol; H2O 9: triethylamine / toluene / 1 h / 20 °C 10: triethylamine; 4-(dimethylamino)pyridine / toluene / 3.5 h / 80 °C 11: 90 percent / trifluoroacetic acid / CH2Cl2 / 7.5 h / 20 °C View Scheme

1.1: iPr2NEt / 24 h / 20 °C 2.1: KOH / methanol / 0.5 h / 20 °C 2.2: Bu3SnH; PdCl2(PPh3)2 / tetrahydrofuran / 1 h / 0 °C 2.3: N-bromosuccinimide / tetrahydrofuran / 0.5 h / 20 °C 3.1: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C View Scheme

1.1: Me2AlCl; Bu3SnH / CH2Cl2 / 3 h / -78 °C 2.1: iPr2NEt / 24 h / 20 °C 3.1: KOH / methanol / 0.5 h / 20 °C 3.2: Bu3SnH; PdCl2(PPh3)2 / tetrahydrofuran / 1 h / 0 °C 3.3: N-bromosuccinimide / tetrahydrofuran / 0.5 h / 20 °C 4.1: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C View Scheme

1: 92 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 18.5 h / 20 °C 2: 83 percent / CF3CO2H / tetrahydrofuran; H2O / 22 h / 20 °C 3: 96 percent / 4-(dimethylamino)pyridine; camphorsulfonic acid; dicyclohexylcarbodiimide / CH2Cl2 / 14 h / 20 °C 4: 19 percent / CH3CO2H / propan-2-ol; H2O 5: triethylamine / toluene / 1 h / 20 °C 6: triethylamine; 4-(dimethylamino)pyridine / toluene / 3.5 h / 80 °C 7: 90 percent / trifluoroacetic acid / CH2Cl2 / 7.5 h / 20 °C View Scheme

1: sodium hydroxide; H2O / methanol; tetrahydrofuran View Scheme

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C 1.2: 99 percent / 4-(dimethylamino)pyridine / toluene / 1 h 2.1: 85 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 120 h / 20 °C 3.1: 95 percent / N,N-diisopropylethylamine / CH2Cl2 / 1 h / 20 °C 4.1: 97 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 5.1: 77 percent / {[P(c-hexyl)3](1,3-dimesitylimidazolidin-2-yl)Ru(=CHPh)Cl2} / CH2Cl2 / 24 h / 20 °C 6.1: 90 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1.1: 99 percent / NaOH / methanol; tetrahydrofuran; H2O / 12 h / 20 °C 2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C 2.2: 99 percent / 4-(dimethylamino)pyridine / toluene / 1 h 3.1: 85 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 120 h / 20 °C 4.1: 95 percent / N,N-diisopropylethylamine / CH2Cl2 / 1 h / 20 °C 5.1: 97 percent / DDQ / CH2Cl2; H2O / 1 h / 20 °C 6.1: 77 percent / {[P(c-hexyl)3](1,3-dimesitylimidazolidin-2-yl)Ru(=CHPh)Cl2} / CH2Cl2 / 24 h / 20 °C 7.1: 90 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C View Scheme