Synthesis of azetidines by electrophilic selenium-induced cyclization of homoallylic benzylamines

Article abstract of DOI:10.1016/S0040-4039(97)00028-2

Homoallyl benzylamines prepared by allylation of the corresponding N-benzylimines, have been subjected to a selenium-induced cyclization under various conditions. At room temperature. the 4-exo and the 5-endo modes are competitive. In acetonitrile, the azetidine has been isolated as the major cyclization product, especially for homoallylamines derived from ketimines. With an excess or selenium reagent, 3-halopyrrolidines have been obtained.