1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C 1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C 2.1: BH3*THF / tetrahydrofuran / 4 h / Heating 2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating 3.1: 94 percent / methanol / 22 h / Heating 4.1: TFAA; TFA / toluene / 15 h / Heating 5.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating View Scheme

1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C 1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C 2.1: BH3*THF / tetrahydrofuran / 4 h / Heating 2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating 3.1: 94 percent / methanol / 22 h / Heating 4.1: TFAA; TFA / toluene / 15 h / Heating 5.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating View Scheme

1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C 1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C 2.1: BH3*THF / tetrahydrofuran / 4 h / Heating 2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating 3.1: 94 percent / methanol / 22 h / Heating 4.1: TFAA; TFA / toluene / 15 h / Heating 5.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating View Scheme