potassium dioxotetrahydroxoosmate(VI); potassium carbonate; dihydroquinidine 9-O-(9'-phenanthryl) ether hydrochloride; potassium hexacyanoferrate(III) in water; tert-butyl alcohol T=0°C; 18 h; enantioselective oxidation; further alkenes investigated; Product distribution;

hydrogenchloride in tetrahydrofuran Ambient temperature;

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating;

bis(η5-cyclopentadienyl)titanium dichloride; 2-methylpropane-2-thiol in tetrahydrofuran Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: With ozone in methanol; dichloromethane T=-78°C; 2: With sodium tetrahydroborate in methanol; dichloromethane T=-78°C; 0.25 h;

phosphate buffer in di-isopropyl ether T=10°C; 12 h; porcine pancreas lipase; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1.1: nBuLi / tetrahydrofuran; hexane / 4 h / -78 - -40 °C 1.2: 51 percent / tetrahydrofuran; hexane / 12 h / -40 °C 2.1: 89 percent / N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH2Cl2 / 4 h / 0 °C 3.1: molecular sieves 4 Angstroem; (R)-Me-CBS; borane-dimethyl sulfide / tetrahydrofuran; toluene / -30 °C 4.1: pyridine; DMAP / 12 h 5.1: hydrogen; Lindlar catalyst / hexane / 2 h 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: NaBH4 / methanol; CH2Cl2 / 0.25 h / -78 °C View Scheme

1.1: molecular sieves 4 Angstroem; (R)-Me-CBS; borane-dimethyl sulfide / tetrahydrofuran; toluene / -30 °C 2.1: pyridine; DMAP / 12 h 3.1: hydrogen; Lindlar catalyst / hexane / 2 h 4.1: ozone / methanol; CH2Cl2 / -78 °C 4.2: NaBH4 / methanol; CH2Cl2 / 0.25 h / -78 °C View Scheme

1.1: 89 percent / N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH2Cl2 / 4 h / 0 °C 2.1: molecular sieves 4 Angstroem; (R)-Me-CBS; borane-dimethyl sulfide / tetrahydrofuran; toluene / -30 °C 3.1: pyridine; DMAP / 12 h 4.1: hydrogen; Lindlar catalyst / hexane / 2 h 5.1: ozone / methanol; CH2Cl2 / -78 °C 5.2: NaBH4 / methanol; CH2Cl2 / 0.25 h / -78 °C View Scheme

1.1: pyridine; DMAP / 12 h 2.1: hydrogen; Lindlar catalyst / hexane / 2 h 3.1: ozone / methanol; CH2Cl2 / -78 °C 3.2: NaBH4 / methanol; CH2Cl2 / 0.25 h / -78 °C View Scheme