1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme

1.1: (Ipc)2BH / tetrahydrofuran / -78 - -10 °C / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / 20 °C / Inert atmosphere 3.2: 3 h / Inert atmosphere 4.1: tetrahydrofuran; methanol / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve 5.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere 6.1: boron tribromide / dichloromethane / 16 h / 0 °C / Reflux; Inert atmosphere View Scheme

sodium hydroxide; (-)-(Ipc)2BH; dihydrogen peroxide 1.) THF, -65 to -78 deg C; Multistep reaction;

1: With (Ipc)2BH in tetrahydrofuran T=-20 - -18°C; 2: With dihydrogen peroxide; sodium hydroxide

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 5: 82 percent / TEA, DMAP / CH2Cl2 6: Dess-Martin reagent, t-BuOH / CH2Cl2 7: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 8: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C 9: 89 percent / BCl3 / CH2Cl2 / -78 °C View Scheme

1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 3.1: NaH / tetrahydrofuran / 1 h / 20 °C 3.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme

(-)-diisopinan-3-ylborane in tetrahydrofuran 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h;

1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C View Scheme

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 5: 82 percent / TEA, DMAP / CH2Cl2 6: Dess-Martin reagent, t-BuOH / CH2Cl2 View Scheme

1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide 4: 60 percent / LiH / dimethylformamide / 2 h / 125 °C 5: 82 percent / TEA, DMAP / CH2Cl2 6: Dess-Martin reagent, t-BuOH / CH2Cl2 7: Zn, TiCl4 / tetrahydrofuran; CH2Cl2 8: 92 percent / aq. HCl / tetrahydrofuran; methanol / 55 °C View Scheme