1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: 100 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: chiral 4-(pyrrolidino)pyridine-derived Fe(II) complex / hexafluorobenzene / 72 h / 20 °C 3.1: diethyl ether / 12 h / 0 °C 4.1: 0.110 g / [Ph(CF3)2CO]SPh2 / CH2Cl2 / 12 h / 20 °C 5.1: 99 percent / H2 / Pd/C / ethanol / 12 h / 20 °C 6.1: oxalic acid dihydrate / acetone; H2O / 2.5 h / 80 °C 7.1: 0.114 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

1: diethyl ether / 12 h / 0 °C 2: 0.110 g / [Ph(CF3)2CO]SPh2 / CH2Cl2 / 12 h / 20 °C 3: 99 percent / H2 / Pd/C / ethanol / 12 h / 20 °C 4: oxalic acid dihydrate / acetone; H2O / 2.5 h / 80 °C 5: 0.114 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

1: 99 percent / H2 / Pd/C / ethanol / 12 h / 20 °C 2: oxalic acid dihydrate / acetone; H2O / 2.5 h / 80 °C 3: 0.114 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

1: chiral 4-(pyrrolidino)pyridine-derived Fe(II) complex / hexafluorobenzene / 72 h / 20 °C 2: diethyl ether / 12 h / 0 °C 3: 0.110 g / [Ph(CF3)2CO]SPh2 / CH2Cl2 / 12 h / 20 °C 4: 99 percent / H2 / Pd/C / ethanol / 12 h / 20 °C 5: oxalic acid dihydrate / acetone; H2O / 2.5 h / 80 °C 6: 0.114 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 81 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.08 h / -78 °C 2.2: 100 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: chiral 4-(pyrrolidino)pyridine-derived Fe(II) complex / hexafluorobenzene / 72 h / 20 °C 4.1: diethyl ether / 12 h / 0 °C 5.1: 0.110 g / [Ph(CF3)2CO]SPh2 / CH2Cl2 / 12 h / 20 °C 6.1: 99 percent / H2 / Pd/C / ethanol / 12 h / 20 °C 7.1: oxalic acid dihydrate / acetone; H2O / 2.5 h / 80 °C 8.1: 0.114 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane T=20°C; 12 h;

1: oxalic acid dihydrate / acetone; H2O / 2.5 h / 80 °C 2: 0.114 g / NaBH(OAc)3 / 1,2-dichloro-ethane / 12 h / 20 °C View Scheme

T=130°C; 1 h;

triethylamine in tetrahydrofuran T=80°C; 48 h; Yield given;

aluminum oxide; potassium fluoride; potassium fluoride on basic alumina in acetonitrile T=100°C; 0.166667 h;