D-glucose; (S)-imine reductase from Streptomyces sp. GF3546; NADPH in aq. phosphate buffer; N,N-dimethyl-formamide T=30°C; pH=7; 18 h; Enzymatic reaction; Kinetics; enantioselective reaction;

lithium diisopropyl amide in tetrahydrofuran 1.) 0 deg C, 2.) -78 deg C, 1 h;

1: 1.) lithium diisopropylamide / 1.) THF, -20 deg C, 15 min, 2a.) -20 deg C, 1.5 h, 2b.) -10 deg C, 0.5 h 2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2a.) -78 deg C, 2 h, 2b.) -40 deg C, 1 h, 2c.) 25 deg C, 16 h 3: 36 percent / NaBH4 / methanol / 3 h / 25 °C 4: 1.) lithium diisopropylamide, 2.) water / THF 5: 1.) lithium diisopropylamide / 1a.) THF, -78 deg C, 1 h, 1b.) -60 deg C, 1 h, 2a.) -78 deg C, 1 h, 2b.) 25 deg C, 1 h 6: 21 percent / Al-Hg, H2O / tetrahydrofuran / 6 h / 25 °C 7: LiAlH4 / diethyl ether / 8 h / 25 °C View Scheme

n-butyllithium; diisopropylamine in tetrahydrofuran; hexane 2 h; -80 deg C to rt;

ZnCl2*Et2O; sodium cyanoborohydride in tetrahydrofuran; ethanol T=25°C; 20 h;

sodium

1: NCS / CCl4 / Heating 2: NaOMe / methanol / 15 h / Ambient temperature View Scheme

sodium tetrahydroborate; lithium diisopropyl amide Yield given. Multistep reaction. Yields of byproduct given;

sodium tetrahydroborate; lithium diisopropyl amide Yield given. Multistep reaction. Yields of byproduct given;

triethylamine in N,N-dimethyl-formamide room temperature -> 50 deg C;