methyloxirane in ethanol; water

ammonium sulfate; tyrosine phenol lyase; ammonium chloride in diethyl ether T=30°C; pH=8; aq. phosphate buffer; optical yield given as percent ee;

1: H2 / Pd/C / CH2Cl2 2: aq. Na2CO3 / acetonitrile View Scheme

1: 67 percent / AlCl3 / nitrobenzene / 6 h / 100 °C 2: 74 percent / SOCl2 / Heating 3: 93 percent / aq. Na2CO3 / diethyl ether / 3 h / 25 °C 4: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 5: mCPBA / CH2Cl2 / 40 °C 6: 453 mg / NH3 / CH2Cl2; methanol / 1 h 7: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 8: H2 / Pd/C / CH2Cl2 9: aq. Na2CO3 / acetonitrile View Scheme

1: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 2: mCPBA / CH2Cl2 / 40 °C 3: 453 mg / NH3 / CH2Cl2; methanol / 1 h 4: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 5: H2 / Pd/C / CH2Cl2 6: aq. Na2CO3 / acetonitrile View Scheme

1: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 2: H2 / Pd/C / CH2Cl2 3: aq. Na2CO3 / acetonitrile View Scheme

1: 74 percent / SOCl2 / Heating 2: 93 percent / aq. Na2CO3 / diethyl ether / 3 h / 25 °C 3: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 4: mCPBA / CH2Cl2 / 40 °C 5: 453 mg / NH3 / CH2Cl2; methanol / 1 h 6: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 7: H2 / Pd/C / CH2Cl2 8: aq. Na2CO3 / acetonitrile View Scheme

1: 93 percent / aq. Na2CO3 / diethyl ether / 3 h / 25 °C 2: 60 percent / K2CO3; (n-Bu)4NI / dimethylformamide / 6 h / 20 °C 3: mCPBA / CH2Cl2 / 40 °C 4: 453 mg / NH3 / CH2Cl2; methanol / 1 h 5: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 6: H2 / Pd/C / CH2Cl2 7: aq. Na2CO3 / acetonitrile View Scheme

1: mCPBA / CH2Cl2 / 40 °C 2: 453 mg / NH3 / CH2Cl2; methanol / 1 h 3: 61 percent / K2CO3 / dimethylformamide / 6 h / 25 °C 4: H2 / Pd/C / CH2Cl2 5: aq. Na2CO3 / acetonitrile View Scheme

1: 0.396 g / K2CO3; n-Bu4NI / dimethylformamide / 20 °C 2: 0.21 g / H2 / Pd/C / methanol / 24 h View Scheme