potassium tert-butylate in tetrahydrofuran T=0 - 20°C; Inert atmosphere;

1: 1-(tert-butoxy-carbonyl)piperidine With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in diethyl ether; hexane T=-78°C; 3 h; 2: With C12H26N2O in diethyl ether; hexane T=-78 - -40°C; 1.5 h; 3: allyl bromide optical yield given as percent eeFurther stages;

1: 1-(tert-butoxy-carbonyl)piperidine With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in diethyl ether; cyclohexane T=-78°C; 3 h; Inert atmosphere; 2: With C12H24N2O(2-)*2Li(1+) in diethyl ether; cyclohexane T=-45°C; 3 h; Inert atmosphere; 3: 3-chloroprop-1-ene optical yield given as percent eeenantioselective reactionFurther stages;

1: With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in diethyl ether; cyclohexane T=-78°C; 3 h; Inert atmosphere; 2: With C12H24N2O(2-)*2Li(1+) in diethyl ether; cyclohexane T=-45°C; 3 h; Inert atmosphere; 3: With 3-chloroprop-1-ene in diethyl ether; cyclohexane T=-78°C; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

sodium hydroxide in dichloromethane; water T=0 - 23°C; 16 h; optical yield given as percent ee;

1: DMAP / tetrahydrofuran / Ambient temperature 2: 1,4-dicyanonaphthalene, methyl viologen / acetonitrile / 10 h / Irradiation 3: TiCl4 / CH2Cl2 / 4 h / -78 °C 4: 82 percent / Li / liquid ammonia; tetrahydrofuran / 1 h / -33 °C 5: K2CO3 / tetrahydrofuran; H2O View Scheme

1: 1,4-dicyanonaphthalene, methyl viologen / acetonitrile / 10 h / Irradiation 2: TiCl4 / CH2Cl2 / 4 h / -78 °C 3: 82 percent / Li / liquid ammonia; tetrahydrofuran / 1 h / -33 °C 4: K2CO3 / tetrahydrofuran; H2O View Scheme

potassium carbonate in tetrahydrofuran; water

1: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 0 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1: N,N-dimethyl-formamide / 36 h / 50 °C 2: triethylamine / dichloromethane / 3 h / Inert atmosphere 3: toluene-4-sulfonic acid / tetrahydrofuran; water / 20 °C 4: Grubb's 2nd generation catalyst / dichloromethane / 6 h / 50 °C / Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h 6: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 0 °C / Inert atmosphere 7: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme