1: 1.) t-BuLi / 1.) THF, pentane, -78 - (-50) deg C, 20 min, 2.) THF, pentane, -50 deg C - room temperature 2: 91 percent / NaBH4 / methanol / 5 h / -10 °C View Scheme

1: With borane; cyclohexene in pentane T=-78°C; 2: With ethanolamine; acetic acid

1: With diisobutylaluminium hydride in hexane T=-78 - 20°C; Inert atmosphere; 2: With iodine in tetrahydrofuran; hexane T=-78 - 20°C; 1.5 h; Inert atmosphere; optical yield given as percent de;

Multistep reaction;

Yield given. Multistep reaction;

1.1: Pd(PPh3)4 / benzene / 25 °C 1.2: 90 percent / CuI; Et3N / 30 h / 25 °C 2.1: 86 percent / PPh3Br2 / CH2Cl2; pyridine / from 0 degC to r.t. 3.1: 87 percent / methanol / 100 °C 4.1: 59 percent / n-BuLi / diethyl ether / 25 °C View Scheme