Chlorine Atom Transfer Radical 6‐exo Cyclizations of Carbamoyldichloroacetate‐Tethered Alkenes, Enol Acetates and α,β‐Unsaturated Nitriles Leading to Morphans

Abstract

AbstractThe CuI‐mediated atom transfer radical cyclization of amino‐tethered dichloromalonamides and electron‐rich, electron‐poor, and nonactivated double bonds is a useful methodology for the synthesis of 2‐azabicyclo[3.3.1]nonanes. A study of the reaction conditions and the scope of the process is reported. Cyclopropane ring formation was observed from the resulting 1,3‐dichlorides in some morphan substrates using either CuI, Pd, or Zn.