silver(l) oxide in water 48 h; Ambient temperature; Title compound not separated from byproducts;

1: MCPBA / CH2Cl2 2: aq. Py View Scheme

sulfuric acid in methanol 4 h; Inert atmosphereReflux;

pyridine

(i) Ag2O, (ii) (deacetylation); Multistep reaction;

[Ir(cycloocta-1,5-diene)2]tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (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; hydrogen in dichloromethane T=25°C; P=37503.8 Torr; 12 h; Reagent/catalyst; enantioselective reaction;

C29H41IrN3O(2+)*C32H12BF24(1-); hydrogen in dichloromethane T=25°C; P=37503.8 Torr; 24 h; enantioselective reaction;

1: imidazole / dimethylformamide / 10 h 2: 1.) lithium bis(trimethylsilyl)amide, 2.) hexamethylphosphoric triamide / 1.) THF, from -78 deg C to 0 deg C, 1 h, 2.) from -78 deg C to RT, 2 h 3: 1.) lithium bis(trimethylsilyl)amide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2.) from -78 deg C to RT, 2 h 4: 95 percent / 40percent aq. HF / acetonitrile / 4 h / Ambient temperature View Scheme

1: PBr3 / diethyl ether / 1 h / Ambient temperature 2: dimethylformamide / 24 h / Ambient temperature 3: 91 percent / DIBAH / tetrahydrofuran; hexane / 0.17 h / -20 °C 4: 56 percent / BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -78 °C 5: 45 percent / Na, dibenzo<18>crown-6 / liquid ammonia; tetrahydrofuran / 0.03 h / -78 °C View Scheme