ethanol; nickel T=20°C; P=2206.5 Torr; Hydrogenation;

1: sodium cyanoborohydride; trifluoroacetic acid / methanol / 2.5 h / 0 - 20 °C 2: toluene / 5 h / Reflux View Scheme

1: NaBH4 / methanol / 3.5 h / 0 - 20 °C 2: benzene / 10 h / 20 °C 3: 55 percent / 4-toluenesulfonic acid / toluene / Heating View Scheme

1: 3-(4-chlorobut-2-enyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one With samarium diiodide in tetrahydrofuran T=20°C; 0.333333 h; Inert atmosphere; 2: N-(furan-2-ylmethylene)benzylamine in tetrahydrofuran T=80°C; Inert atmosphereSealed tube; optical yield given as percent dediastereoselective reaction;