phosphate buffer; dihydrogen peroxide; chiral Al(salalen) in methanol T=20°C; 24 h;

phosphate buffer; dihydrogen peroxide; chiral Al(salalen) in methanol T=20°C; 24 h;

titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; alpha,alpha-dimethylbenzyl hydroperoxide in dichloromethane T=-23°C; further reag.: t-BuOOH; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

alpha,alpha-dimethylbenzyl hydroperoxide; 4 A molecular sieve; titanium(IV) isopropylate; (3S,4S)-2,2,5,5-tetramethyl-3,4-hexanediol in toluene T=-20°C; Oxidation; 60 h; Title compound not separated from byproducts;

(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 toluene 1 h;

1: dihydrogen peroxide / 2,2,2-trifluoroethanol; water / 0 - 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: potassium carbonate / dichloromethane / 20 h / 20 °C / Inert atmosphere 2: dihydrogen peroxide / 2,2,2-trifluoroethanol; water / 0 - 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: With (1R,2S)-2-ammonio-1,2-diphenylethanol p-tert-butylbenzoate in hexane 4 h; 2: With Daicel Chiralcel OB-H in hexane; isopropyl alcohol Further stages.;