C88H90N2O6P2; dihydrogen peroxide; magnesium sulfate in cyclohexane; water T=20°C; 2 h; 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;

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: 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;