1: DIBAL / tetrahydrofuran; toluene / 20 °C 2: H2 / chiral iridium catalyst / CH2Cl2 / 24 h / 20 °C / 15001.2 Torr View Scheme

((C8H12)Ir((C6H5)2PCH2C7H8N2C6H5))(1+)*B(C6H3(CF3)2)4(1-)=((C8H12)Ir((C6H5)2PCH2C7H8N2C6H5))(B(C6H3(CF3)2)4); hydrogen in dichloromethane T=40°C; P=75007.5 Torr; 72 h; Autoclave; optical yield given as percent ee;

1: DIBAL / tetrahydrofuran; toluene / 20 °C 2: 48 percent / pyridine / 24 h / 20 °C 3: H2 / chiral Iridium catalyst / CH2Cl2 / 12 h / 20 °C / 22501.8 Torr View Scheme

sodium hydride in N,N-dimethyl-formamide 2 h;

1: DIBAL / tetrahydrofuran; toluene / 20 °C 2: 48 percent / pyridine / 24 h / 20 °C View Scheme