1: sodium t-butanolate; C22H31N2O7Rh / toluene / 0.5 h / 80 °C / |Inert atmosphere 2: sodium peroxoborate tetrahydrate; water / tetrahydrofuran / 0.3 h / 20 °C View Scheme

bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; C17H20O; water; triethylamine in 1,4-dioxane T=50°C; 0.5 h; Inert atmosphere;

bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; R-solphos; water; triethylamine in 1,4-dioxane T=50°C; 15 h; Inert atmosphere; enantioselective reaction;

C26H36F6FeN6O6S2; dihydrogen peroxide; (S)-2-(4-isobutylphenyl)propionic acid in acetonitrile T=-30°C; 1 h; Reagent/catalyst;

1: 44 percent / 10percent aq. NaOH / aq. ethanol / 2 h / Heating 2: aq. KOH / 8 h / 195 °C View Scheme

water; sodium hydroxide in ethanol T=20°C; 12 h;

Multi-step reaction with 8 steps 2: KOH / ethanol3: diethyl ether4: 80 percent / KHCO3 / dimethylformamide / 5 h / 20 °C5: 91 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 5 h / 0 - 20 °C6: sodium azide / dimethylformamide / 12 h / 80 °C7: 0.07 g / H2 / Pd/C / ethyl acetate / 760 Torr8: 94 percent / aq. LiOH / tetrahydrofuran / 1 h / 70 °C  

Multi-step reaction with 8 steps 2: KOH / ethanol3: diethyl ether4: 0.18 g / KHCO3 / dimethylformamide / 12 h / 20 °C5: 82 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 5 h / 0 - 20 °C6: sodium azide / dimethylformamide / 12 h / 80 °C7: 0.32 g / H2 / Pd/C / ethyl acetate / 12 h / 760 Torr8: 100 percent / aq. LiOH / tetrahydrofuran / 1 h / 70 °C  

With  osmium(VIII) oxide; methanesulfonamide; (9-O-indolinylcarbamoyl)dihydroquinidine (DHQD-IND); potassium carbonate; potassium hexacyanoferrate(III) in  water; toluene; tert-butyl alcohol T=0°C;  Yield given. Yields of byproduct given. Title compound not separated from byproducts;   

With  osmium(VIII) oxide; methanesulfonamide; (9-O-indolinylcarbamoyl)dihydroquinidine (DHQD-IND); potassium carbonate; potassium hexacyanoferrate(III) in  water; toluene; tert-butyl alcohol T=0°C;  Yield given. Yields of byproduct given. Title compound not separated from byproducts;