thionyl chloride in dichloromethane T=0 - 20°C; Inert atmosphere;

1.1: magnesium / tetrahydrofuran / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 1.3: 20 °C / Inert atmosphere 2.1: thionyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

1: 1-(α-chlorobenzyl)naphthalene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; 2: cyanoacetic acid ethyl ester With sodium hydride in tetrahydrofuran; mineral oil 3 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;