1: With ozone in methanol T=-78°C; 0.5 h; 2: With dimethylsulfide in methanol T=-78 - 20°C; Inert atmosphere; 3: With hydrogenchloride; water T=100°C; 48 h; Sealed vessel; optical yield given as percent de;

Hydrolysis;

1: With NosE gene from Escherichia coli; nicotinamide adenine dinucleotide; anhydrous zinc sulfate; glycine in water T=42°C; pH=10; 5 h; 2: With NosF gene from Escherichia coli in water pH=10; 0.25 h; Further stages.;

1.1: trifluoroacetic acid / CH2Cl2 / 16 h / 20 °C 1.2: 84 percent / Dowex-50W resin [H(+)-form] / H2O 2.1: NosE gene from Escherichia coli; β-NAD; ZnSO4 / glycine / H2O / 5 h / 42 °C / pH 10 2.2: NosF gene from Escherichia coli / H2O / 0.25 h / pH 10 View Scheme

1: With ozone in methanol T=-78°C; 0.5 h; 2: With dimethylsulfide in methanol T=-78 - 20°C; 3: With hydrogenchloride; water in methanol T=110°C; 48 h; Sealed tube; optical yield given as percent de;

1.1: chromic acid / aq. HCl / 1 h / 80 °C 2.1: NosE gene from Escherichia coli; β-NAD; ZnSO4 / glycine / H2O / 5 h / 42 °C / pH 10 2.2: NosF gene from Escherichia coli / H2O / 0.25 h / pH 10 View Scheme

1.1: trifluoroacetic acid / CH2Cl2 / 20 °C 1.2: 88 percent / Dowex-50W resin [H(+)-form] / H2O 2.1: chromic acid / aq. HCl / 1 h / 80 °C 3.1: NosE gene from Escherichia coli; β-NAD; ZnSO4 / glycine / H2O / 5 h / 42 °C / pH 10 3.2: NosF gene from Escherichia coli / H2O / 0.25 h / pH 10 View Scheme

1: 64 percent 2: 90 percent 3: 91 percent View Scheme

1: CHCl3 / 2 h / Heating 2: lead nitrate, Et3N / CHCl3 / 87 h / Ambient temperature 3: 75 percent / CH2Cl2 / 16 h / Ambient temperature 4: 1.) potassium hexamethyldisilazide (KHMDS) / 1.) THF, toluene, -78 deg C, 1 h, 2.) THF, toluene, 3 h 5: 24 percent / LiAlH4 / tetrahydrofuran / 4 h / -78 °C 6: 88 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 7: 90 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme

1: 75 percent / CH2Cl2 / 16 h / Ambient temperature 2: 1.) potassium hexamethyldisilazide (KHMDS) / 1.) THF, toluene, -78 deg C, 1 h, 2.) THF, toluene, 3 h 3: 24 percent / LiAlH4 / tetrahydrofuran / 4 h / -78 °C 4: 88 percent / PPh3, CBr4, iPr2NEt / tetrahydrofuran / 1 h / Ambient temperature 5: 90 percent / CF3CO2H / CH2Cl2 / 16 h View Scheme