1: With bis(1,5-cyclooctadiene)nickel (0); Ipr.HCl; cesium fluoride in toluene T=30 - 80°C; Inert atmosphere; 2: With water in diethyl ether; toluene T=20°C; 1 h; Inert atmosphere;

1: With [RhCl(η2:η2-cycloocta-1,5-diene)]2; potassium carbonate in toluene T=90 - 110°C; 2: With hydrogenchloride in water; toluene

1: (2-naphthyl)MgBr With Et2AlBr in tetrahydrofuran T=0 - 20°C; Inert atmosphere; 2: With titanium(IV) isopropylate; (S)-(minus;)-1,1'-bi-2-naphthol in toluene T=0°C; 0.5 h; Inert atmosphere; 3: acetophenone Further stages;

1: phenyl-magnesium bromide With Et2AlBr in tetrahydrofuran T=0 - 20°C; Inert atmosphere; 2: With titanium(IV) isopropylate; (S)-(minus;)-1,1'-bi-2-naphthol in toluene T=0°C; 0.5 h; Inert atmosphere; 3: 2-acetonaphthalene Further stages;

bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; chlorobenzene; cesium fluoride; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride in toluene T=80°C; 1.5 h; Inert atmosphere;

titanium(IV) isopropylate; magnesium bromide; (1S,2R,4R,1'R,2'R,1''S,2''R,4''R)-N-{trans-2'-[2''-hydroxy-7'',7''-dimethylbicyclo[2.2.1]hept-1''-ylmethylsulfonamino]cyclohexyl}-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethanesulfonamide in toluene T=0°C; 12 h; Inert atmosphere;

[Rh(OH)(cycloocta-1,5-diene)]2; (+/-)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis{bis[2,6-bis(trifluoromethyl)-4-pyridyl]phosphine} in water; toluene T=40°C; 1 h; Inert atmosphere;

1.1: magnesium sulfate / diethyl ether / 20 °C 2.1: bis(1,5-cyclooctadiene)nickel (0); Ipr.HCl; cesium fluoride / 1,4-dioxane; toluene / 0.5 h / 20 °C / Inert atmosphere 2.2: 60 - 80 °C / Inert atmosphere View Scheme