hydrogen; [Rh(cod)(R-Binapine)]BF4 in methanol T=65°C; P=21752.2 - 24752.5 Torr; 18.25 h; Product distribution / selectivity;

hydrogenchloride in isopropyl alcohol T=55 - 65°C; 0.5 h; Product distribution / selectivity;

hydrogen; [(S)-Xyl-P-Phos RuCl(p-cymene)]Cl in methanol T=80 - 85°C; P=18751.9 - 23252.3 Torr; 21 h; Product distribution / selectivity;

hydrogen; palladium on activated charcoal T=3°C; P=7600 Torr; 3 h; Yield given;

1: in tetrahydrofuran; water T=20°C; 3 h; 2: With hydrogenchloride T=20°C;

hydrogen; triethylamine in methanol

1.1: 90 percent / imidazole / CH2Cl2 / 5 h / 0 - 20 °C 2.1: 90 percent / tetrahydrofuran / 6 h / 20 °C 3.1: 97 percent / (DHQD)2PHAL; K3Fe(CH)6; K2CO3 / OsO4 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 4.1: 98 percent / dibutyltin oxide; NEt3 / CH2Cl2 / 0.75 h / 20 °C 5.1: 90 percent / AcOH / H2O; tetrahydrofuran / 10 h / 60 °C 6.1: 98 percent / NaI / acetone / 6 h / Heating 7.1: H2O; tetrahydrofuran / 3 h / 20 °C 7.2: 90 percent / methanolic HCl / 20 °C View Scheme

1: H2, <Rh(COD)Cl>2, (2R,4R)-N-(methylcarbamoyl)-4-(dicyclohexylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine, triethylamine / methanol / 20 h / 50 °C / 15200 Torr 2: H2 / 10percent Pd/C / ethanol / 3 h / 50 °C / 7600 Torr View Scheme

1.1: 90 percent / tetrahydrofuran / 6 h / 20 °C 2.1: 97 percent / (DHQD)2PHAL; K3Fe(CH)6; K2CO3 / OsO4 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 3.1: 98 percent / dibutyltin oxide; NEt3 / CH2Cl2 / 0.75 h / 20 °C 4.1: 90 percent / AcOH / H2O; tetrahydrofuran / 10 h / 60 °C 5.1: 98 percent / NaI / acetone / 6 h / Heating 6.1: H2O; tetrahydrofuran / 3 h / 20 °C 6.2: 90 percent / methanolic HCl / 20 °C View Scheme

1.1: 97 percent / (DHQD)2PHAL; K3Fe(CH)6; K2CO3 / OsO4 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 2.1: 98 percent / dibutyltin oxide; NEt3 / CH2Cl2 / 0.75 h / 20 °C 3.1: 90 percent / AcOH / H2O; tetrahydrofuran / 10 h / 60 °C 4.1: 98 percent / NaI / acetone / 6 h / Heating 5.1: H2O; tetrahydrofuran / 3 h / 20 °C 5.2: 90 percent / methanolic HCl / 20 °C View Scheme