1: (3R)-hept-1-ene-4,6-diyn-3-ol With copper(l) iodide; tetrabutyl-ammonium chloride; potassium carbonate in N,N-dimethyl-formamide T=20°C; 0.25 h; 2: (Z)-1-chlorodec-2-ene in N,N-dimethyl-formamide T=20°C; 8 h; Further stages.;

immobilised Candida antarctica lipase B; water in acetone T=20°C; pH=7.4; 43 h; aq. phosphate bufferEnzymatic reaction; optical yield given as percent eeenantioselective reaction;

1.1: 86 percent / H2; quinoline; KOH / Lindlar catalyst / ethanol / 16 h / atmospheric pressure 2.1: 81 percent / PPh3; CCl4 / 16 h / 80 °C 3.1: Bu4N(1+)*Cl(1-); K2CO3; CuI / dimethylformamide / 0.25 h / 20 °C 3.2: 69 percent / dimethylformamide / 8 h / 20 °C View Scheme

1.1: 91 percent / triethylamine; 4-(dimethylamino)pyridine / 2 h / 20 °C 2.1: Candida antarctica B lipase; Na2HPO4 buffer / 0.5 h / 20 °C / pH 7.5 / Enzymatic reaction 3.1: Bu4N(1+)*Cl(1-); K2CO3; CuI / dimethylformamide / 0.25 h / 20 °C 3.2: 69 percent / dimethylformamide / 8 h / 20 °C View Scheme

1.1: 81 percent / PPh3; CCl4 / 16 h / 80 °C 2.1: Bu4N(1+)*Cl(1-); K2CO3; CuI / dimethylformamide / 0.25 h / 20 °C 2.2: 69 percent / dimethylformamide / 8 h / 20 °C View Scheme

1.1: 0.74 g / H2SO4 / tetrahydrofuran; H2O / 3 h / 80 °C 2.1: Bu4N(1+)*Cl(1-); K2CO3; CuI / dimethylformamide / 0.25 h / 20 °C 2.2: 69 percent / dimethylformamide / 8 h / 20 °C View Scheme

1.1: Candida antarctica B lipase; Na2HPO4 buffer / 0.5 h / 20 °C / pH 7.5 / Enzymatic reaction 2.1: Bu4N(1+)*Cl(1-); K2CO3; CuI / dimethylformamide / 0.25 h / 20 °C 2.2: 69 percent / dimethylformamide / 8 h / 20 °C View Scheme

1: CuCl, NH2OH*HCl, EtNH2 / methanol / 0 °C 2: Bu4NF / tetrahydrofuran / Ambient temperature View Scheme