chloro-trimethyl-silane; sodium iodide in 1,4-dioxane T=80°C;

water; lithium diisopropyl amide in tetrahydrofuran 1.) -75 deg C, 1.5 h, 2.) -75 deg C, 2 h;

1: 1) lithium diisopropylamide, 2) I2, 3) H2O / 1) THF, -75 deg C, 4 h, 2) THF, -75 deg C, 1 h, 3) THF, -75 to 0 deg C 2: 1) n-butyllithium/DABCO chelate, 2) I2, 3) H2O / 1) Et2O, -60 deg C, 2 h, 2) THF, -60 deg C, 1 h, 3) THF, -75 to 0 deg C View Scheme

copper (I) cyanide; lithium tert-butylate in 1,4-dioxane T=100°C; 12 h; Inert atmosphere; regioselective reaction;