borane in tetrahydrofuran T=25°C; 1 h;

triethylamine in tetrahydrofuran; 1,4-dioxane

sodium tetrahydroborate; lithium chloride in tetrahydrofuran; ethanol Ambient temperature; Yield given;

porcine pancreatic lipase in hexane; toluene T=37°C; pH=7; 3 h; aq. phosphate bufferEnzymatic reaction; optical yield given as percent ee;

1: 9.15 g / diisopropylethylamine / CH2Cl2 / 2 h 2: 13.61 g / imidazole / dimethylformamide / 6 h 3: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 4: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 5: CuBr-SMe2 / tetrahydrofuran; diethyl ether / 1 h / -40 °C 6: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: 13.61 g / imidazole / dimethylformamide / 6 h 2: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 3: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 4: CuBr-SMe2 / tetrahydrofuran; diethyl ether / 1 h / -40 °C 5: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 2: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 3: CuBr-SMe2 / tetrahydrofuran; diethyl ether / 1 h / -40 °C 4: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 2: CuBr-SMe2 / tetrahydrofuran; diethyl ether / 1 h / -40 °C 3: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: CuBr-SMe2 / tetrahydrofuran; diethyl ether / 1 h / -40 °C 2: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran 2: tetrahydrofuran View Scheme