lithium aluminium tetrahydride in tetrahydrofuran T=20°C; Inert atmosphere;

sodium hydroxide in ethanol 0.5 h; Ambient temperature;

1: With sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate in tetrahydrofuran T=25 - 70°C; hydroboration; 2: With sodium hydroxide; dihydrogen peroxide T=0°C; Oxidation;

Lipase R derived from Pennicillium roqueforti lipase in cyclopentyl methyl eher; water T=5°C; 72 h; Resolution of racemateInert atmosphereEnzymatic reaction; optical yield given as percent ee;

Lipase R derived from Pennicillium roqueforti in di-isopropyl ether T=35°C; 72 h; Resolution of racemateInert atmosphereEnzymatic reaction; optical yield given as percent ee;

Lipase A12 derived from Apergillus niger in di-isopropyl ether T=35°C; 240 h; Resolution of racemateInert atmosphereEnzymatic reaction; optical yield given as percent ee;

1.1: 93 percent / aq. acetic acid / 1.5 h / 65 - 70 °C 2.1: 82 percent / triethylamine / CH2Cl2 / 1.5 h / 20 °C 3.1: 20.9 percent / BF3*OEt2 / tetrahydrofuran / 60 h / 45 - 50 °C 4.1: 85 percent / aq. sodium hydroxide / methanol / 80 °C 5.1: 93 percent / pyridine 6.1: 95 percent / sodium hydride in 60 percent oil / tetrahydrofuran / 0 - 20 °C 7.1: 69 percent / magnesium bromide etherate / diisopropyl ether / 20 °C 8.1: 46 percent / zinc powd. / ethanol / Heating 9.1: sodium borohydride,; BF3*OEt2,; 9-BBN / tetrahydrofuran / 25 - 70 °C 9.2: 43 percent / aq. NaOH,; 30 percent H2O2 / 0 °C View Scheme

1.1: 78 percent / dimethyl sulfoxide,; oxalyl chloride,; triethylamine / CH2Cl2 / 0.83 h / -78 °C 2.1: 93 percent / aq. acetic acid / 1.5 h / 65 - 70 °C 3.1: 82 percent / triethylamine / CH2Cl2 / 1.5 h / 20 °C 4.1: 20.9 percent / BF3*OEt2 / tetrahydrofuran / 60 h / 45 - 50 °C 5.1: 85 percent / aq. sodium hydroxide / methanol / 80 °C 6.1: 93 percent / pyridine 7.1: 95 percent / sodium hydride in 60 percent oil / tetrahydrofuran / 0 - 20 °C 8.1: 69 percent / magnesium bromide etherate / diisopropyl ether / 20 °C 9.1: 46 percent / zinc powd. / ethanol / Heating 10.1: sodium borohydride,; BF3*OEt2,; 9-BBN / tetrahydrofuran / 25 - 70 °C 10.2: 43 percent / aq. NaOH,; 30 percent H2O2 / 0 °C View Scheme

1.1: 82 percent / triethylamine / CH2Cl2 / 1.5 h / 20 °C 2.1: 20.9 percent / BF3*OEt2 / tetrahydrofuran / 60 h / 45 - 50 °C 3.1: 85 percent / aq. sodium hydroxide / methanol / 80 °C 4.1: 93 percent / pyridine 5.1: 95 percent / sodium hydride in 60 percent oil / tetrahydrofuran / 0 - 20 °C 6.1: 69 percent / magnesium bromide etherate / diisopropyl ether / 20 °C 7.1: 46 percent / zinc powd. / ethanol / Heating 8.1: sodium borohydride,; BF3*OEt2,; 9-BBN / tetrahydrofuran / 25 - 70 °C 8.2: 43 percent / aq. NaOH,; 30 percent H2O2 / 0 °C View Scheme

1: 67 percent / p-toluenesulfonic acid / toluene / 5 h / Heating 2: 89 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 14 percent / various solvent(s) / 24 h / Ambient temperature; Candida cylindracea lipase 4: 84 percent / NaOH / ethanol / 0.5 h / Ambient temperature View Scheme