1: H2 / Lindlar / methanol 2: 87 percent / t-BuOOH, d-diethyl tartrate, Ti(O-i-Pr)4 / CH2Cl2 / -20 °C 3: 79 percent / NaIO4 / RuCl3 / CCl4; acetonitrile; H2O 4: 87 percent / petroleum ether / 40 h / 25 °C 5: 90 percent / pyridine 6: 95 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 7: 86 percent / DCC, 4-pyrrolidinopyrridine / CH2Cl2 / 5 h / 25 °C 8: Bu4NF / tetrahydrofuran / 3 h / 25 °C 9: Ph3P, EtOsCN=NCO2Et / 20 h / 25 °C 10: 70 percent / MeOH / NaOMe / 2 h / 0 °C View Scheme

1: 1-but-3-ynyloxy-2,2-dimethyl-1,1-diphenyl-1-silapropane With n-butyllithium in tetrahydrofuran T=-78 - 0°C; 1 h; 2: formaldehyd in tetrahydrofuran T=20°C; 3 h;

1: tert-butylchlorodiphenylsilane With n-butyllithium in tetrahydrofuran; pentane T=-78°C; 0.5 h; Inert atmosphere; 2: formaldehyd in tetrahydrofuran; pentane T=20°C; 2 h; Inert atmosphere;

1.1: 99 percent / imidazole; 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / 20 °C 2.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: 72 percent / diethyl ether; hexane / 18 h / 20 °C View Scheme

diisobutylaluminium hydride in dichloromethane T=-78°C;

1: n-BuLi / hexane / -78 °C 2: DIBAL-H / CH2Cl2 / -78 °C View Scheme

1: With sodium bis(2-methoxyethoxy)aluminium dihydride in diethyl ether; toluene T=0 - 20°C; 1.08333 h; 2: With ethyl acetate in diethyl ether; toluene T=0°C; 0.166667 h; 3: With iodine in diethyl ether; toluene T=-78 - 20°C; 2 h;

1: 99 percent / CBr4, Ph3P / CH2Cl2 / 0 °C 2: 75 percent / CuI, nBu4NI, Na2CO3 / dimethylformamide / Ambient temperature 3: 89 percent / H2, Ni(OAc)2, NaBH4 / Ambient temperature 4: 1.) MsCl, Et3N, 2.) NaI / 1.) CH2Cl2, RT, 2.) acetone, reflux 5: 99 percent / acetonitrile / Heating 6: 63 percent / n-BuLi, HMPA / tetrahydrofuran / -78 °C 7: 90 percent / n-Bu4NF*THF / acetic acid / Ambient temperature 8: MnO2 / diethyl ether / Ambient temperature View Scheme

carbon tetrabromide; triphenylphosphine in dichloromethane T=0°C;

sodium bis(2-methoxyethoxy)aluminium dihydride in diethyl ether T=0°C;