1: iodobenzene; diethylaluminium chloride With n-butyllithium in diethyl ether; hexane T=-55 - -20°C; 1 h; 2: 3-methylcyclopent-2-en-1-one With copper(I) thiophene-2-carboxylate; 1,1-bis(3,5-dimethylphenyl)-N,N-bis((S)-1-(naphthalen-2-yl)ethyl)phosphinamine in diethyl ether; hexane T=-10°C; Michael addition; optical yield given as percent ee;

silver hexafluoroantimonate; C21H22Cl2N2O2Pd in methanol; water T=40°C; 24 h; Inert atmosphere; optical yield given as percent ee;

[RhCl(η2:η2-cycloocta-1,5-diene)]2; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl in tetrahydrofuran; 1,4-dioxane T=5°C; Michael condensation; Inert atmosphere; optical yield given as percent eeenantioselective reaction;

in water; dimethyl sulfoxide 24 h; Heating;

Ag2[(S,S)-C3N2H2Ph2(C6H2)(CH3)3(C6H4C6H4O)]2; copper(II) bis(trifluoromethanesulfonate) in tetrahydrofuran T=-50°C; 48 h; Reactivity; Reagent/catalyst; optical yield given as percent eeenantioselective reaction;

1.1: 85 percent / Ph3P; 1H-imidazole; I2 / diethyl ether; acetonitrile / 3 h / 20 °C 2.1: BuLi; diisopropylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -25 - 0 °C 2.2: 54 percent / HMPA / tetrahydrofuran; hexane / 1 h / 20 °C 3.1: 76 percent / KOH / methanol / 0.17 h / 0 °C 4.1: 57 percent / Rh2(OAc)4 / CH2Cl2 / 3 h / 0 °C 5.1: 68 percent / dimethylsulfoxide; H2O / 24 h / Heating View Scheme

1.1: BuLi; diisopropylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -25 - 0 °C 1.2: 54 percent / HMPA / tetrahydrofuran; hexane / 1 h / 20 °C 2.1: 76 percent / KOH / methanol / 0.17 h / 0 °C 3.1: 57 percent / Rh2(OAc)4 / CH2Cl2 / 3 h / 0 °C 4.1: 68 percent / dimethylsulfoxide; H2O / 24 h / Heating View Scheme

1: 76 percent / KOH / methanol / 0.17 h / 0 °C 2: 57 percent / Rh2(OAc)4 / CH2Cl2 / 3 h / 0 °C 3: 68 percent / dimethylsulfoxide; H2O / 24 h / Heating View Scheme

1: 59 percent / Rh2(OAc)4 / CH2Cl2 / 0.5 h / 23 °C 2: 68 percent / dimethylsulfoxide; H2O / 24 h / Heating View Scheme

1: 57 percent / Rh2(OAc)4 / CH2Cl2 / 3 h / 0 °C 2: 68 percent / dimethylsulfoxide; H2O / 24 h / Heating View Scheme