1: cyclohexenon With N-(((2S,4R)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl)methyl)-1,1,1-trifluoromethanesulfonamide in dichloromethane T=20°C; 1 h; 2: N-(phenylseleno)phthalimide in dichloromethane T=20°C; 24 h; Product distribution / selectivity;

potassium fluoride on basic alumina T=20 - 60°C; 14.5 h; Inert atmosphere;

hydrogenchloride; chloro-trimethyl-silane; lithium diisopropyl amide Yield given. Multistep reaction;

1: 99 percent / CeCl3*H2O, NaBH4 / methanol / 0.17 h 2: 93 percent / DMAP / CH2Cl2 / 24 h / Heating 3: tributyltin hydride, AIBN / benzene / 8 h / Heating View Scheme

1: 99 percent / CeCl3*H2O, NaBH4 / methanol / 0.17 h 2: 93 percent / DMAP / CH2Cl2 / 24 h / Heating 3: tributyltin hydride, AIBN / benzene / 8 h / Heating View Scheme