(R,R,aR,aR)-[RuCl(NO)((CH3)2C6H8(NCHC10H5(O)C10H6Ph)2)]; water; oxygen in ethyl acetate T=25°C; 48 h; Visible light irradiation; optical yield given as percent eeenantioselective reaction;

dihydrogen peroxide in water T=25°C; 0.0833333 h; chloroperoxidase (CPO), citrate buffer pH 5; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(1S,2R)-(+)-N,N-dimethylephedrinium bis(trifluoromethanesulfon)imidate in dichloromethane T=140°C;

(1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; sodium hydroxide in dichloromethane; water; toluene T=0°C; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

in diethyl ether; benzene Ambient temperature;

1: potassium carbonate / dichloromethane / 20 h / 20 °C / Inert atmosphere 2: dihydrogen peroxide / dichloromethane; 2,2,2-trifluoroethanol; water / 72 h / 20 °C 3: (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; sodium hydroxide / dichloromethane; water; toluene / 0 °C / Inert atmosphere View Scheme

1: dihydrogen peroxide / dichloromethane; 2,2,2-trifluoroethanol; water / 72 h / 20 °C 2: (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; sodium hydroxide / dichloromethane; water; toluene / 0 °C / Inert atmosphere View Scheme

1: SOCl2 / benzene / Ambient temperature 2: pyridine / diethyl ether / 1 h / Ambient temperature 3: 75 percent / diethyl ether; benzene / Ambient temperature View Scheme

1: 1.) aq. NaNO2, H2SO4, 2.) Cu, SO2 / 1.) 0 deg C, 2.) -25 deg C, 1 h 2: SOCl2 / benzene / Ambient temperature 3: pyridine / diethyl ether / 1 h / Ambient temperature 4: 75 percent / diethyl ether; benzene / Ambient temperature View Scheme

1: With titanium(IV) isopropylate in dichloromethane 0.166667 h; Inert atmosphere; 2: With dihydrogen peroxide in water Inert atmosphere; 3: Inert atmosphere; Kinetics; Concentration; optical yield given as percent eeenantioselective reaction;