lithium aluminium tetrahydride in diethyl ether T=-50°C;

1: (4-methyl-1-phenylpent-3-en-2-yl)(phenyl)sulfane With LiDBB in tetrahydrofuran T=-11°C; 2: chloro-trimethyl-silane in tetrahydrofuran T=-11°C;

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 1.2: 77 percent / TMEDA / tetrahydrofuran; hexane / 3 h / -78 - 20 °C 2.1: lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / -11 °C 2.2: 21 percent / tetrahydrofuran / -11 °C View Scheme

1.1: pyridine; tri-n-butylphosphine / 20 °C 1.2: 94 percent / NaBH4 / 1 h 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 2.2: 77 percent / TMEDA / tetrahydrofuran; hexane / 3 h / -78 - 20 °C 3.1: lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / -11 °C 3.2: 21 percent / tetrahydrofuran / -11 °C View Scheme

1: 56 percent / Et3N / diethyl ether / -20 °C 2: 65 percent / LiAlH4 / diethyl ether / -50 °C View Scheme

1: 56 percent / Et3N / diethyl ether / -20 °C 2: 65 percent / LiAlH4 / diethyl ether / -50 °C View Scheme