sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide in methanol; water; acetonitrile T=0 - 20°C; 3 h; Inert atmosphere;

1.1: sodium dihydrogenphosphate; sodium chlorite; dihydrogen peroxide / methanol; water; acetonitrile / 3 h / 0 - 20 °C / Inert atmosphere 2.1: methanol / diethyl ether; toluene / 3 h / 0 - 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / diethyl ether / 1 h / -100 °C / Inert atmosphere 3.2: 1 h / -100 °C / Inert atmosphere 4.1: dimethylsulfide borane complex / hexane / 0 °C / Inert atmosphere 4.2: 1 h / Inert atmosphere; Reflux 5.1: triethylamine / dichloromethane / 2 h / Inert atmosphere 6.1: 1.5 h / 20 °C / Inert atmosphere 7.1: sodium hydroxide / dichloromethane; water / Inert atmosphere 8.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 3 h / Inert atmosphere; Reflux View Scheme

sodium tetrahydroborate in methanol Inert atmosphere;

With  (S)-[α,α-bis(3,5-bistrifluoromethyl)phenyl]-2-pyrrolidine methanol trimethylsilyl ether; benzoic acid in  chloroform T=-50°C; aza-Michael reaction; 22 h;  Inert atmosphere;  optical yield given as percent eeenantioselective reaction;  Show Experimental Procedure