Lewis acid-mediated unprecedented ring-opening rearrangement of 2-aryl-N-tosylazetidines to enantiopure (E)-allylamines.
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.
Ghorai
Manas K
MK
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. mkghorai@iitk.ac.in
Kumar
Amit
A
Das
Kalpataru
K