1: With borane-THF in tetrahydrofuran T=20°C; 0.166667 h; Inert atmosphere; 2: With copper(II) bis(trifluoromethanesulfonate) in tetrahydrofuran 2 h; Inert atmosphere; regioselective reaction;

1.1: borane-THF / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: sodium periodate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate / dichloromethane; water / 4 h / 0 - 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h 3.2: 3 h / 0 °C / Inert atmosphere View Scheme

1.1: borane-THF / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: sodium periodate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate / dichloromethane; water / 4 h / 0 - 20 °C View Scheme