1: allyl bromide With magnesium in diethyl ether 2: (S)-2-methyl-1-butyl bromide With dilithium tetrachlorocuprate in tetrahydrofuran; diethyl ether T=-70 - 20°C;

1.1: pyridine / 3 h / 0 - 5 °C 2.1: lithium bromide / N,N-dimethyl-formamide / 1 h / 60 °C 3.1: magnesium / diethyl ether 3.2: -70 - 20 °C View Scheme

1.1: lithium bromide / N,N-dimethyl-formamide / 1 h / 60 °C 2.1: magnesium / diethyl ether 2.2: -70 - 20 °C View Scheme

zirconocene dichloride; ammonium chloride 1.) Et2O, 20-25 deg C, 4 h, 2.) H2O, 0 deg C; Yield given. Multistep reaction;

zirconocene dichloride; ammonium chloride 1.) Et2O, 20-25 deg C, 2.) H2O, 0 deg C; reactants ratio and reaction time dependence; Product distribution;

1: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 2: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 3: 66 percent / liquid ammonia / 6 h 4: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 5: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol View Scheme

1: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 2: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 3: 66 percent / liquid ammonia / 6 h View Scheme

sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h; Yield given. Multistep reaction;

1: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 2: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 3: 66 percent / liquid ammonia / 6 h 4: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 5: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 6: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme