1: (MeO)3B, NaH / 1,2-dimethoxy-ethane / 16 h / Heating 2: H2SO4 / 48 h / Ambient temperature 3: PBr3 / diethyl ether / 1 h / Ambient temperature View Scheme

1: (MeO)3B, NaH / 1,2-dimethoxy-ethane / 16 h / Heating 2: H2SO4 / 48 h / Ambient temperature View Scheme

1: lithium borohydride / tetrahydrofuran / 12 h / 20 °C / |Inert atmosphere 2: sulfuric acid / methanol / 4 h / |Inert atmosphere; |Reflux 3: C29H41IrN3O(2+)*C32H12BF24(1-); hydrogen / dichloromethane / 24 h / 25 °C / 37503.8 Torr View Scheme

1: lithium borohydride / tetrahydrofuran / 12 h / 0 - 25 °C / |Inert atmosphere 2: sulfuric acid / 4 h / |Reflux; |Inert atmosphere 3: (1S,2R,4S,5R)-2-((1S)-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidine; [Ir(cycloocta-1,5-diene)2]tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen / dichloromethane / 12 h / 25 °C / 37503.8 Torr View Scheme

1: 77 percent / borane-tetrahydrofurane complex / tetrahydrofuran / -10 - 20 °C 2: 67 percent / phosphorus tribromide / CCl4 / 1 h / 20 °C 3: diisobutyl aluminum hydride / toluene; hexane / 1 h / -78 °C View Scheme

1: (MeO)3B, NaH / 1,2-dimethoxy-ethane / 16 h / Heating 2: H2SO4 / 48 h / Ambient temperature 3: PBr3 / diethyl ether / 1 h / Ambient temperature 4: dimethylformamide / 24 h / Ambient temperature 5: 91 percent / DIBAH / tetrahydrofuran; hexane / 0.17 h / -20 °C 6: 56 percent / BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -78 °C 7: 45 percent / Na, dibenzo<18>crown-6 / liquid ammonia; tetrahydrofuran / 0.03 h / -78 °C View Scheme