Opening of azetidinium ions with C-nucleophiles

The nucleophilic opening of functionalized azetidinium ions by C-nucleophiles was screened. Malonate and cyanide anions reacted in a highly regio- and chemoselective way leading to functionalized pure amines. The success of this reaction was found to be highly dependent on the basicity of the involved nucleophiles and the competitive reactions induced by too basic reagents were identified.