Diphenyl-lt;(((1S,2R,3R)-pinan-3-yl)-methylamino)-ethylgt;-phosphin; hydrogen; cobalt in ethanol T=50°C; P=9120 Torr; 16 h;

1: 1.) Cl2, glacial AcOH / 1.) CCl4, 30-35 deg C, 5 min, 2.) acetone, reflux, 15 min 2: 91 percent / PCl5 / chlorobenzene / 1 h / 60 - 80 °C 3: 92 percent / Cl2 / CHCl3; CCl4 / 72 h / 20 - 25 °C 4: 92 percent / 1.) H2O, 2.) aq. NaClO4 / dioxane / 1 h / Heating 5: 95 percent / 1.) PCl5, 2.) aq. NaClO4 / chlorobenzene / 0.5 h / Heating 6: 40 percent / aq. NaOH / methanol / 0.17 h / Heating View Scheme

1: triethylamine / 3 h / |Reflux 2: boron trifluoride diethyl etherate; [bis(acetoxy)iodo]benzene / 1,2-dichloro-ethane / 2 h / |Reflux View Scheme

Diphenyl-lt;(((1S,2R,3R)-pinan-3-yl)-methylamino)-ethylgt;-phosphin; hydrogen; cobalt in ethanol T=50°C; P=9120 Torr; 16 h;

1: acetic acid anhydride 2: benzene View Scheme

chloroformic acid ethyl ester; triethylamine in benzene 0.25 h; Heating;

triethylamine in acetonitrile 1 h; Ambient temperature;

hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (R,R)-BICP in tetrahydrofuran T=20°C; P=750.075 Torr; 24 h;

hydrogen; triethylamine; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in ethanol; benzene 24 h; Ambient temperature;

hydrogen; lt;Rh((R)-cycphos)(NBD)gt;PF6 in ethyl acetate T=25°C; P=38000 Torr; effects of catalysts, pressure, temperature and solvents dependence of the optical yields, effect of added of NEt3;