Ru(II)-rac-BINAP; hydrogen in tetrahydrofuran T=75°C; P=10343.2 Torr; 16 h; Reagent/catalyst;

1: 81 percent / L-Selectride; LiBr / tetrahydrofuran / -78 °C 2: 52 percent / DDQ / CH2Cl2 / 20 °C 3: 53 percent / TiCl4 / CH2Cl2; tetrahydrofuran / 20 °C 4: H2 / 20 percent Pd(OH)2/C / tetrahydrofuran; methanol; H2O / 750.06 Torr View Scheme

1: 90 percent / L-Selectride / tetrahydrofuran / -78 °C 2: 80 percent / DMAP / CH2Cl2 / 20 °C 3: 80 percent / H2 / Pd(OH)2/C / methanol; tetrahydrofuran / 6 h / 20 °C View Scheme