Mechanistic Study of SmI2‐Mediated Reformatsky Reaction for Macrolactam Formation Using a Cyclopropyl Group as a Probe

Abstract

AbstractA mechanistic study using a cyclopropylmethyl radical clock as a probe to investigate the formation of a macrolactam ring via an SmI2‐mediated intramolecular Reformatsky reaction is experimentally explored. The results of our study indicate that the key SmIII‐enolate intermediate is formed by cleavage of a C−Br bond in an anion‐mediated β‐elimination, and then eventually undergoes an intramolecular aldol condensation to form the macrolactam ring.