Lewis Acid-Mediated Unprecedented Ring-Opening Rearrangement of 2-Aryl-<i>N</i>-tosylazetidines to Enantiopure (<i>E</i>)-Allylamines

Abstract

A highly efficient strategy for Cu(OTf)2-mediated ring-opening of 2-aryl-N-tosylazetidines in polar and coordinating solvents followed by an unprecedented rearrangement to substituted achiral and chiral (E)-allylamines (ee >99%) is reported. The methodology has been applied for the synthesis of gamma-unsaturated-beta-amino acids. A plausible mechanism for the rearrangement is also described.