1: 84 percent / N,N,N',N'-tetramethylguanidine / tetrahydrofuran 2: 49 percent / urea-H2O2 complex; TFAA / acetonitrile 3: H2 / (R,R)-[Rh(Et-DUPHOS)COD(COD)]BF4 / methanol / 48 °C / 2327.23 Torr 4: 92 percent / Zn; aq. NH4Cl / tetrahydrofuran / 20 °C 5: LiOH / tetrahydrofuran; H2O 6: H2; aq. HCl / Pd/C / methanol View Scheme

1: LiOH / tetrahydrofuran; H2O 2: H2; aq. HCl / Pd/C / methanol View Scheme

1: 92 percent / Zn; aq. NH4Cl / tetrahydrofuran / 20 °C 2: LiOH / tetrahydrofuran; H2O 3: H2; aq. HCl / Pd/C / methanol View Scheme

1.1: triethylamine 2.1: 80.4 percent / m-CPBA / CHCl3 / 4 h / 20 °C 3.1: acetic anhydride / 3 h / 100 °C 3.2: 84 percent / conc. HCl / tetrahydrofuran / 48 h / 25 °C 4.1: 80 percent / Et3N / tetrahydrofuran / 8 h / 0 - 20 °C 5.1: butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 5.2: tetrahydrofuran; hexane / 4 h / -78 °C 6.1: 90 percent / aq. HCl / acetonitrile / 36 h / 20 °C 7.1: 65 percent / aq. NaOH / 6 h / Heating View Scheme

1.1: 80.4 percent / m-CPBA / CHCl3 / 4 h / 20 °C 2.1: acetic anhydride / 3 h / 100 °C 2.2: 84 percent / conc. HCl / tetrahydrofuran / 48 h / 25 °C 3.1: 80 percent / Et3N / tetrahydrofuran / 8 h / 0 - 20 °C 4.1: butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: tetrahydrofuran; hexane / 4 h / -78 °C 5.1: 90 percent / aq. HCl / acetonitrile / 36 h / 20 °C 6.1: 65 percent / aq. NaOH / 6 h / Heating View Scheme

sodium hydroxide 6 h; Heating;

1: 93 percent / sodium iodide / acetone / 2.5 h / 23 °C 2: 1.) lithium diisopropylamide, lithium chloride / 1) hexane, THF, 0 deg C, 20 min; 2) THF, hexane, -78 deg C, 3 h, -45 deg C, 3 h 3: aq. NaOH / 6 h / Heating View Scheme

tyrosine phenol-lyase from Citrobacter freundii; pyridoxal 5'-phosphate; ammonium chloride T=25°C; pH=8.0 - 8.2; 120 h;

1: 89 percent / 45percent HBr / acetic acid / 3 h / Heating 2: 59 percent / Na / ethanol; tetrahydrofuran / 18 h / Heating 3: 1.) 6M NaOH / 1.) EtOH, room temperature, 1.5 h, 2.) dioxane, reflux, 1.5 h 4: 36 percent / α-chymotrypsin, NH4OAc, pH 6.9, 1 M NH4OH / dimethylformamide; H2O / 2 h / Ambient temperature 5: 85 percent / 5M HCl / 3.5 h / Heating View Scheme

1: 1.) 6M NaOH / 1.) EtOH, room temperature, 1.5 h, 2.) dioxane, reflux, 1.5 h 2: 36 percent / α-chymotrypsin, NH4OAc, pH 6.9, 1 M NH4OH / dimethylformamide; H2O / 2 h / Ambient temperature 3: 85 percent / 5M HCl / 3.5 h / Heating View Scheme