osmium(VIII) oxide; N-methyl-2-indolinone in tetrahydrofuran T=20°C; Oxidation; Dihydroxylation; 48 h;

boron trifluoride diethyl etherate in dichloromethane T=-64°C;

halohydrin dehalogenase HheC (Agrobacterium radiobacter AD1) in N,N-dimethyl-formamide T=20°C; pH=8.1; 48 h;

in further solvent(s) argon-filled glovebox, durene, bibenzyl, 130°C, 23h; product detd. by GC and IR;

1: 2,3,4,6-tetra-OAc-D-manopyranose; propargyl alcohol With copper(II) bis(trifluoromethanesulfonate) in acetonitrile T=20°C; 2 h; 2: D-galactal With trimethylsilylazide; copper in acetonitrile T=20°C; 9 h; optical yield given as percent dediastereoselective reaction;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=0 - 20°C;

1: 87 percent / lipase PS (Amano) / tetrahydrofuran; hexane / 72 h / 20 °C 2: 100 percent / 0.05M MeONa / methanol / 20 °C View Scheme

potassium hydroxide; 4-phenylbut-3-en-2-one; tris(triphenylphosphine)ruthenium(II) chloride in diethylene glycol dimethyl ether 20 h; Heating;

1: mCPBA / CH2Cl2 / 3 h / 20 °C 2: 1.56 g / p-TsOH*H2O / benzene / 3 h / Heating 3: 90 percent / CeCl3*7H2O; NaBH4 / methanol / 10 h / 0 °C 4: 94 percent / pyridine / CH2Cl2 / 12 h / 20 °C 5: 51 percent / Lipase AK immobilized on Celite, Pseudomonas sp. Amano / acetone; aq. phosphate buffer / 24 h / 20 °C / pH 7.2 / Enzymatic reaction View Scheme