triethylamine; copper dichloride; palladium dichloride T=25°C; P=760 Torr; 75 h;

1: SOCl2 / 3.25 h / Heating 2: acetonitrile / 8 h / Ambient temperature; Irradiation View Scheme

1: (methoxycarbonylmethyl)methyldiphenylphosphonium chloride With potassium hexamethylsilazane in tetrahydrofuran Wittig reaction; 1 h; Inert atmosphere; 2: 2-chloro-benzaldehyde in tetrahydrofuran T=-78°C; Wittig reaction; Inert atmosphereCooling with acetone-dry ice; optical yield given as percent dediastereoselective reaction;

(p-trifluoromethyl)phenylsilane; tris(n-octyl)phosphine oxide; N-ethyl-N,N-diisopropylamine; 4-nitro-benzoic acid in toluene T=100°C; Wittig Olefination; 24 h; Inert atmosphereSealed tubeSchlenk technique; Overall yield = 81 percent; Overall yield = 159 mg; diastereoselective reaction;

in water T=20°C; Wittig reaction; 0.0833333 h; Title compound not separated from byproducts.;

in acetonitrile 8 h; Ambient temperatureIrradiation; Yield given;

1.1: toluene / 0 - 20 °C / Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / Inert atmosphere 2.2: -78 °C / Inert atmosphere; Cooling with acetone-dry ice View Scheme